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As a former resident of Elkton in Cecil County Maryland this article covers fun things to do in and around Elkton as well as some of my favorite local places.  And you won’t need to cross state lines into neighboring Delaware or Pennsylvania or even county lines. There isn’t anything on this list that will require you to drive more than an hour to Baltimore and call it a “Thing to do in Elkton.” Everything in this article is either in Elkton or within Cecil County.

Elkton and Maryland’s Upper Chesapeake Bay region offers plenty of outdoor activities, historic places, terrific restaurants, quaint small towns and so much more that there is no need for you to travel to these other locales.

Elkton Painted Elk

**Disclaimer: This was a hosted stay, however, all opinions are my own. I strive to provide my readers with my most authentic sentiments.

Where are Elkton, Cecil County, and the Upper Chesapeake?

If you are not familiar with Elkton or Cecil County or only aware of the better-known Eastern Shore, let me give you the lay of the land.  Cecil County Maryland is a rural area located in the Northeast corner of the state. It’s situated at the head of the Chesapeake Bay and borders Pennsylvania, Delaware, and the Susquehanna River. Because of its unique location, it’s easily accessible from I-95 and only a 45-minute drive from both Baltimore and Philadelphia.

Cecil County map

One of the nice aspects of Elkton and greater Cecil County besides its easy accessibility is that it offers both the best of rural and bay life. Cecil County still has significant farmland with u-pick orchards, wineries, hiking trails, and horseback riding. But if nautical is more your speed you can find an abundance of that as well. There is plenty of kayaking, crabbing, and fishing too.

Main Street, Elkton MD

Elkton, Known as the “Wedding Capital of the East Coast”

Elkton Maryland has historically been known as the place young lovers go to elope or for a quickie marriage. Even my great-grandparents who resided in Baltimore were wed in Elkton in 1917. Perhaps one of your relatives made the trip to Elkton to tie the knot too. 

Through much of the 20th Century Elkton had been known as the “Wedding Capital of the East Coast.” In the early part of the century, states began imposing wait times for marriage, requiring marriage licenses and mandatory blood tests. In many states, divorced people could not marry.

Wedding Chapel. Elkton MD

Maryland was one of the few states that did not have these restrictions. Couples would arrive by train to Elkton, the County Seat of Cecil County, and head to Courthouse for a no-wait marriage license. Once that formality was out of the way they just needed to choose for one of 20 marriage chapels located on the town’s Main Street.

During the first half of the 20th Century ministers in Elkton would perform up to 40 weddings a day. Today there is only one chapel remaining but sadly they stopped performing weddings in 2017.

Like many small towns across America, Elkton’s Main Street fell on hard times with the opening of mega-stores like Walmart and Home Depot. Bail bonds people and attorneys became the predominant business in town.

Downtown Elkton MD

Today, Elkton’s Main Street has undergone a revitalization, and small businesses occupy most of the storefronts. Visitors will find vibrant Main Street with restaurants, antique shops, art studios, galleries, and even a small community theatre.

Explore Elkton and the other Surrounding Small Towns

Elkton Maryland and the small towns of greater Cecil County have a long history of agriculture and maritime tradition that is still present today. The area is marked by small rural and bay communities each with its own flavor.

Elkton, the seat of Cecil County, located at the most northeast corner of Maryland is exactly what you would expect, a town that centers around the courts and public services. But it is also a town that remains true to its rural and bay heritage while coalescing as an art community.

Cecil County Arts Alliance Elk

Chesapeake City, Charlestown, Port Deposit, and North East are small towns that were built around the bay and the tributaries that feed the greater Chesapeake. All have strong ties to the water and were instrumental in early American History.

On the south end of the county is Earlville, a very rural section of the county that borders the Elk River. This area is marked by horse farms, wide open spaces, and tributaries such as the Sassafras and Bohemia Rivers that feed the bay.

Stroll Downtown Elkton

Meander down Elkton’s Main Street from Bridge Street to South Street. There are a few stops along the way that should not be missed.

Main and North Streets, Elkton MD

Get acquainted with Chesapeake City

This small colonial hamlet settled in the 17th century is situated on the C and D Canal, a major shipping thoroughfare between the Chesapeake and Delaware Bays built by the Army Corps of Engineers in the early 1900s.

The city’s historic area is on both the National and Maryland Historic Registries. Here you will find both historic colonial and Victorian-era homes, popular restaurants, boutique shops, antique stores, and galleries. This waterfront village is a favorite destination and stopping point for those in the boating community. Chesapeake City has been featured in Travel & Leisure, Coastal Living, and Southern Living.

St. Georges Bridge over the C and D Canal in Chesapeake City, MD

While here, pull up a seat at Pell Garden Park on the waterfront and watch the cargo ships, colorful masted sailboats, and luxury yachts go by. This lovely community park is the site of the Canal Town Brew Fest held in June.

From mid-April through mid-October Chesapeake City Water Tours operates a ferry that runs between the north and south sides of the C and D Canal.

Learn a little bit about the history of the town, the creation of the C and D Canal, and its evolution at the C and D Canal Museum which is located in the original pump house used to control the locks.

North East: The Head of the Bay

Located at the top of the Chesapeake Bay and along the North East River, the charming small town of North East is a bustling tourist area during the summer and a sleepy community the rest of the year.

As you make your way along Main Street, there are a number of places you will want to check out:

North East Chocolates,  Itsy Bitsy Candy Store, North East MD

Main Street, North East, MD

Listed on the National Registry of Historic Places is the Gilpin’s Falls Covered Bridge (North East Road (MD 272) over North East Creek), a wooden covered bridge built in 1860-61 spanning the North East Creek. The bridge is built in Burr Arch Truss design predominantly from Eastern White Pine. It spans 100 feet (30 m) and has a total length of 119 feet. Though no longer in use, it deserves a visit.

Gilpin Covered Bridge near North East MD
By Kjssws – Own work, Public Domain,

Finally, St. Mary Anne’s Episcopal Church and Cemetery (315 S. Main Street), built in 1742 and originally dedicated to St. Mary is an intriguing and historic place to visit. In gratitude to Queen Anne of England who bequeathed a large Bible, a Book of Common Prayer, a silver chalice, and paten to the congregation the parish added Anne to its name.

The colony of Maryland was founded on the principles of religious tolerance intended to ensure religious freedom from persecution for Christian settlers.  Under an Act of the General Assembly in 1692 the Anglican Church (Church of England) became the established church. Saint Mary Anne’s is one of the 15 post-1692 Anglican parishes established in the Province of Maryland.

Saint Mar Anne's Episcopal Church and Cemetery in North East, MD

If you happen to be in the area the first weekend of May you will want to check out St. Mary Anne’s Annual Garden Market, a two-day extravaganza with 50 garden-related vendors, drawing 5000+ people. In addition to flowers, trees, and shrubs you will find natural soaps, fresh produce, pottery plus baked goods.

Explore Tiny Port Deposit

Located on the east bank of the Susquehanna River north of where the river dumps into the Chesapeake Bay, Port Deposit is a delightful place to visit. The entire historic district of this riverside village is listed as a historic district and is on the National Register of Historic Places.

Port Deposit MD

Incorporated in 1824, this tiny hamlet measuring less than two and a half square miles, served as a ferry crossing connecting with Lapidium (now just ruins) on the river’s west bank. The section of the river between Upper Port Deposit and Lapidium was the northernmost point where there were deepwater ports on the Susquehanna. River barges and wagons loaded with cargo would float down the river to this “port of deposit”, where the cargo would then be transferred to ships.

Typical Granite building in Port Deposit MD

The north end of Port Deposit is rich in granite. Throughout the town, you will see it used in many of the distinctive buildings including homes and churches. Older granite and brick buildings line the main street.

The bluffs towering above the town have been terraced and stairways lead between streets. You can see an example of this at what’s known as the Tome Steps, a 75-step granite stairway, built circa 1900, to connect Main Street to the National Historic Tome School for Boys.

Tome Steps Port Deposit MD

Prone to flooding, it’s a miracle this little town even exists. In addition to its interesting architecture and city design, Port Deposit offers some outstanding dining options to suit every taste and occasion.

Additionally, there is a walking path that runs along the river. It’s a beautiful spot to take an evening walk as the setting sun dances across the river.

When leaving Port Deposit, you may want to swing by the Hollywood Casino Perryville and try your luck. Maryland’s first casino, which opened in 2010, boasts 75,000 square feet of gaming floor including slot machines, table games, off-track betting, and barstool sportsbook. Good luck!

Get Artsy in Elkton

In 2006, the State of Maryland awarded the town of Elkton the designation of an “Arts and Entertainment District,” establishing it as an arts community. To further distinguish itself as such, the town and local arts-related enterprises began holding First Friday events.

Area businesses in conjunction with the Elkton Alliance, Cecil County Arts Council, and Cecil College’s Fine Arts and Performing Arts have worked to develop what has come to be known as the Elkton Arts Loop.

Elkton Painted Elk, CCAA

As you look around this town you will find funky painted elks gracing the streets (one on the corner of Main and Bridge Streets and another stands in the perennial garden in front of the Cecil County Art Alliance), murals on the side of buildings, and cheerfully painted parking meters.

In front of the Cecil County Courthouse, you will find a 15-by-5-foot mixed metal sculpture by blacksmith Matthew Harris in honor of late master blacksmith and notable Cecil County artist Alphonsus M. Moolenschot. The sculpture named; “Hammering Heart” is a “flowing sail” topped by a freeform heart.

If you’re attending First Friday, Art Space on Main (138 W Main St) makes a great starting point for the Art Loop. The open workspace at this members-based pottery studio allows you to watch as potters create. Browse the gallery stocked with items by the member artists. In addition to beautiful pieces that will make a statement in your home, you will find pieces that make a thoughtful gift.

If you need an evening free from the kids, every Friday (including First Friday), Art Space on Main (offers Kids Happy Hour from 6 p.m. to 8 p.m. where kids work on a clay project and have pizza and soda.

Pottery at Art Space on Main in elkton Md

Visit the Palette and the Page (120 E Main Street), a female-owned gallery shop featuring works from a roster of local artists, authors and singers/songwriters, and musicians. You will find works in a variety of media including paintings, drawings, photography, lettering art, handcrafted jewelry, finely crafted paper items, ceramics, and turned-wood items. First Fridays often provide an opportunity to meet the artist, listen to live music, and/or attend a book signing.

As you make your way further east, stop in at the Cecil County Arts Council (135 E Main St), a non-profit organization supporting the fine arts in Cecil County. They hold monthly themed exhibits, art classes, and workshops, and provide grant and scholarship opportunities to community residents, organizations, and schools. First Fridays are the perfect time to check out their monthly themed exhibits which are typically quite good.

First Friday activities are from 5 pm to 8 pm. If you go, I recommend parking in the municipal lot off North Street. After 4:30 pm parking is free. From the lot, you can walk to all the participating locations.

Discover Historic Places

Mount Harmon Plantation

A 350-acre tobacco plantation dating back to 1651, Mount Harmon Plantation (600 Mount Harmon Road, Earleville MD) is one of Maryland’s most beautiful and historic Tidewater Plantations. Resting on a peninsula formed by the convergence of the Sassafras River and the Chesapeake Bay, early maps refer to the point as World’s End.

Situated at the end of a two-mile lane flanked by Osage orange trees, is the stately Brick Georgian-style Manor House dating back to 1730. The home’s restoration depicts the colonial period and is furnished with period antiques. The dwelling boasts an exquisite Chippendale staircase railing and a magnificent formal boxwood garden.

Mount Harmon Plantation, Earlville, MD

Friends of Mount Harmon, the property’s stewards, strive to tell the entire story of Mount Harmon Plantations and all the people who lived here. This includes indentured servants, slaves, and tenant farmers.

Visitors can view the original plantation kitchen, see a recreated smokehouse, and stand inside a replica of the sparsely furnished slave quarters.

Plantation Kitchen at Mount Harmon

While you’re here, feel free to walk the grounds. This beautiful waterfront property features a 200-acres nature preserve with 5 miles of trails that meander through meadows, along the waterfront, and through stands of trees.

Guided Tours include the Manor House and Plantation Outbuildings: colonial kitchen, smokehouse, and replica slave quarters are available Thursday to Sunday, from May through October from 10 am to 3 pm with the last tour at 2 pm. Tour Admission: $10 for adults, $8 students/seniors. Members and children under 5 are Free.

Topiary garden at Mount Harmong Plantation, Earlville ND

Day Passes are available daily from 9 am to 5 pm year-round. Day passes permit you to explore the grounds, gardens, picnic areas, miles of scenic nature trails, and 200-acre waterfront Nature Preserve at Mount Harmon. Historic buildings and tours are NOT included. Restroom Facilities Open Seasonally between March 15 and December 15. Day Pass Admission: $10 for adults, $8 students/seniors. Members and children under 5 are Free.

Historic Elk Landing

Historic Elk Landing (590 Landing Lane, Elkton, Maryland), situated at the point where the Little Elk and Big Elk Creeks converge, holds a prominent place in Maryland’s and Mid-Atlantic history. In the three centuries since it was first settled Elk Landing has served many purposes.

Beginning in 1693, the site served as the residence, trading post, and operational hub for Swedish-American trader John Hansson Steelman. The property’s original stone structure known as the John Hanson Steelman Tavern is listed on The National Register of Historic Places.

The Head of Elk is incorporated in 1787. This is the earliest settlement at Elk Landing and what is today known as the Town of Elkton.

JOhn Hanson Steelman Tavern at Historic Elk Landing, Elkton MD
Elk Landing. (2023, March 25). In Wikipedia.

By the early 19th century, Elk Landing is a bustling port. Several ship’s ledgers were stored in the Hollingsworth House documenting the goods being imported and exported through Elk Landing.

During the War of 1812 Elk Landing was the site of Fort Hollingsworth. This small fortification safeguarded Elkton from the fate many small towns along the Chesapeake Bay suffered at the hands of the British Army, making it a historically significant site.

By the late 1800s, Elk Landing was transformed into a boatyard. But by 1910 silting of the Big Elk Creek forced the boat builders to relocate, leading to the property’s decline.

The City of Elkton acquired 42 acres from the Hollingsworth family who had owned the property for over two and a half centuries, in 1999. The following year, they along with The Historic Elk Landing Foundation, Inc., a non-profit organization signed a renewable 99-year lease. The aim of this alliance is to restore the property and operate it as a living history museum.

Today, the grounds at Historic Elk Landing are open to the public from dawn to dusk daily. The 18th-century Hollingsworth House is displayed as it would have appeared in the 19th century and is open for tours (by appointment).

Hollingsworth House at Historic Elk Landing, Elkton MD
By Smallbones – Own work, CC BY-SA 3.0,

Rooms on the home’s upper floor display artifacts of historical significance including letters written by Thomas Jefferson and archeological finds taken from the property during investigations. Two dioramas show the property during different periods. One depicts the property as it would have appeared during the defense of Elkton in the War of 1812, and the other shows the 20th-century boatyard that shared the property.

The grounds are open to the public, from dawn to dusk. Park in the grassy area just to the left of the gate.

House tours are available by appointment. Please call 410-620-6400

Historical Society of Cecil County

Located at 135 East Main Street within the same building as the Cecil County Arts Council is the Historical Society of Cecil County (HSCC). Dedicated to the collection, preservation, and interpretation of artifacts relevant to Cecil County, the HSCC operates as an all-volunteer non-profit organization.

HSCC holds a vast collection of documents including wills, obituaries, land and business records, as well as personal letters that illuminate life in Cecil County through the years. Additionally, you will find an impressive collection of photographs, postcards, slides, negatives, drawings, and more that highlight daily life in Cecil County including businesses and organizations, life on the bay, leisure life, and more. Those doing genealogy research can visit the research library. There is a $5 fee for non-members.

In addition to documents and images, the museum holds a sizable collection of militaria in the Sheriff John F. DeWitt Military Museum, a museum in DeWitt’s memory and dedicated to Cecil County veterans of all wars.

Behind the building is the Rev. Duke Cabin, a late 18th or early 19th-century cabin that was originally located on Bow Street in Elkton and has been a residence, a barbershop, a store, and possibly a textile shop. But its most historically significant purpose was as the residence of Reverend William Duke an Episcopal Priest and schoolmaster of no less than four area schools including Elkton Academy.

Near the cabin are the Gardens at 135. The gardens include those surrounding the main building and the large plot in front of the cabin. That garden began as a community service project at the request of the juvenile court system. Filled with perennials, herbs, and vegetables, the gardens are tended to by volunteers and beautified through donations and grant money. The Gardens at 135 is a true community garden.

Visit the C and D Canal Museum

Located on the south side of the canal in the City of Chesapeake City, the C and D Canal Museum (815 Bethel Rd, Chesapeake City, MD) provides a look at the history of the canal. The museum is situated in the original pump house that controlled the locks of the earliest version of the canal.

Pumphouse at the C and D Canal Museum in Chesapeake City MD
By Acroterion – Own work, CC BY-SA 3.0,

Operated by the U.S. Army Corps of Engineers, the museum features interactive displays. Exhibits include fossils, tools used by canal diggers, as well as the original steam-driven engine and the waterwheel that once controlled the lock system.

Explore the Outdoors

Elkton and the greater Cecil County offer some wonderful hiking, biking, and horseback riding trails for people of all ages and levels. And whether you seek a rural experience or a bayside one, you won’t be disappointed because there are some of each.

Hike, Bike, or Horseback Ride at Fair Hill Nature Reserve

If you are interested in a rural hike or bike ride try the Fair Hill Nature Reserve, a 5,656-acre reserve offering more than 25 miles of trails with varying degrees of difficulty. Some of the trails are mixed-use including walking, biking, and horseback riding.  The trails are part of the Maryland State Parks system.

Horseback riding covered bridge

My recommendation is to walk either the Orange or the Green Trail. Both will lead you to the Fair Hill Nature and Environmental Center and the covered bridge. The Orange Trail is designated as difficult, but I think most people can do it. I believe it gets a more rigorous designation because, unlike the Green Trail, it has a number of spots that are dirt trails with loose stones.

Trek Bike on a rocky trail at Fair Hill recreational Area in Cecil County

These picturesque trails offer varied terrain featuring hills, dirt single track, rocky areas, and streams. Along the way, you will pass ruins dating back to the 1800s and a covered bridge.

Fair Hill is a popular mountain biking destination for people from neighboring states and Maryland alike. That is partially due to its proximity to Delaware and Pennsylvania but it’s also a solid place to ride. Fair Hill hosts NICA races for teams from PA, MD, and NJ.

If you are looking for a mix of wooded trails and sunny fields, then the Red or Blue Trails are for you.

While here, stop by the Fair Hill Nature and Environmental Center. Open Monday-Friday, 8:30 am – 2:30 pm, the center conducts educational programs and tours. The center is a non-profit operated by the Fair Hill Environmental Foundation, Inc.

Fair Hill Nature and Environmental Center. Fair Hill Md

Hike to Turkey Point Lighthouse at Elk Neck State Park

Elk Neck State Park provides a comfortable walk along mostly shady, wooded trails. Perched on 100-foot bluffs above the Elk Neck River you will enjoy stunning views of the Upper Chesapeake Bay area. The walk to the Turkey Point Lighthouse is roughly a mile and an easy stroll.

Additionally, there is one area along the trail that is known to be particularly good for birdwatching. Both hawks and eagles have been spotted here. But even if you don’t get to see any of these majestic birds, the lighthouse and the views are reward enough.

Turkey Point Lighthouse

The Turkey Point Lighthouse Station is listed on the National Register of Historic Places and though only 35 feet tall, it is the third-highest light off the water. This is because it is situated on those towering bluffs above the water.

The light originally fitted with eleven wicks and reflectors has been upgraded several times through the years to include a 4th order Fresnel Lens with a single lamp. The addition of electricity and automation in the 1940s coincided with the retirement of Fannie Salter, the last female lighthouse keeper in the United States. Salter who served from 1925 until her retirement is one of many woman lightkeepers who served at Turkey Point.

View of Chesapeake Bay from Turkey Point State Park

Additionally, Elk Neck State Park offers 250 campsites and 15 cabin rentals. Campsites come equipped with a firepit and bathroom facilities are conveniently located.  The campgrounds are just minutes from the hiking trail at the Turkey Point Lighthouse. Additionally, the park service offers a day-use area which includes a swimming area, canoe/kayak launch, picnic shelters, picnic tables, and grills.

Bike the C and D Canal Recreational Trail

The C and D Canal Recreational Trail offers a different experience than those offered by the Maryland State Park system. This 17-mile 2-state trail beginning in North Chesapeake City runs along the canal to Delaware City in Delaware. These are mixed-use trails for walking, biking, and horseback riding. A walk and a bite to eat along the C and D Canal is a delightful way to spend an afternoon, especially in the fall.

Maryland Delaware State Line with bike in front of marker

Explore two great small towns and enjoy a relaxing bike ride in a single afternoon. Here’s everything you need to know about biking the C and D Canal Trail.

Enjoy Time on the Water

As you can imagine, boating is a favorite pastime on the Chesapeake Bay and is a huge draw to the region. But if you don’t have a boat that doesn’t mean you can’t enjoy a bit of time on the water.

Take the Water Taxi

The brainchild of Wellwood Restaurant’s owner, Larry Metz, the Water Taxi was intended to bring business into the restaurant. The taxi shuttles people staying on the North East River to and from the restaurant located in Charlestown. This allows patrons to enjoy their time without worrying about getting home after a few drinks.

From the North East River

But even if you won’t be enjoying a meal at the Wellwood, you can call and arrange a ride on the Water Taxi. Captain Jim will pick you up and show you the sites along the shoreline. The water taxi is also available for charter and is popular with bachelors and bachelorettes.

Kayak or Stand Up Paddle Board on the North East Creek and River

Kayaking and Stand Up Paddleboarding both offer summer fun, especially on a hot day. Bay Ventures Outfitters located on the shores of the North East River in North East, offers a wide range of activities on the water including sit-on-top kayaks (single and tandem) and Stand up Paddleboard rentals. They can be rented for use at their location or they offer free delivery within a 12-mile radius for rentals over $150.

In addition to rentals, they offer kayaks and SUP tours. Looking for something fun to do? Try SUP Yoga. And for Independence Day bring the kids and enjoy a Fireworks Paddle.

Sail Boat on the North East river

I had the pleasure of going out for a paddle with Bay Ventures owner, Kelly Benson. The tour began with a safety review including the proper fit of my personal floatation device/lifejacket (PFD).

We started with an easy paddle along the North East Creek and chatted about environmental issues centered around the Chesapeake Bay. He told me about Project Clean Stream a program that brings volunteers together to pick up trash from local streams, creeks, rivers, parks, and neighborhoods with the goal of developing a healthier and more sustainable relationship with the bay. Followed by spending some time on the river where he pointed out important landmarks along the shoreline.

North East Community Park

Located on the North East River and the upper banks of the Chesapeake Bay, this is a lovely community park with a gazebo, a playground for the kids, a boardwalk where locals fish, and the Upper Bay Museum. It is a beautiful place to take in the bay breezes and enjoy an afternoon with the family. This park offers plenty of recreational activities for everyone.

North East Community Park

While there, stop by the Upper Bay Museum (219 West Walnut Street, North East) which features artifacts related to the hunting, boating, and fishing heritage of the region. The museum also hosts the Upper Shore Decoy Show, one of the longest-running shows of its kind in the nation.

Additionally, the museum is home to the Chesapeake Wooden Boat Builders School.

The museum is only open Saturdays from Memorial Day thru Labor Day. Admission is free. 

Experience a bit of AgTourism

Go on an AgVenture at Milburn Orchards

Whether you are looking for a U-pick adventure or a day with the kids at the Big Backyard, fun will be had by all at Milburn Orchards (1495 Appleton Road, Elkton).

Summertime in rural Cecil County offers a bounty of farm fresh produce simply not found at your local grocery store or even your neighborhood Whole Foods. U-pick fruit season begins in early to mid-June (check website for specifics) with the first harvest of Bing and white cherries. In addition to cherries, Milburn Orchards offer, U-pick blueberries, grapes, blackberries, and red raspberries throughout the summer and apples and grapes into the fall.

Apples at Milburn Orchards

The Barnyard is always open for petting and feeding all your farm favorites, goats, roosters, ducks, and more. Climb on the Tractor Tire Tower or visit the barnyard playground. But dog owners are asked to leave Fido home.

The orchard hosts not just one but a series of Fall Festival weekends that are fun for the whole family. This seven-weekend affair brings all things associated with autumn; pumpkins, hayrides, apples, the changing of the leaves to their seasonal hues of orange, crimson, and gold, and let’s not forget trick or treating.

Big Backyard at Milburn Orchards in Elkton MD

Regardless of what you do during your AgVenture be sure to visit the Orchard View Deck, a snack bar featuring finger food and hand-scooped Hershey’s Ice Cream.  

And don’t leave without stopping by the Farm Market and Country Bake Shoppe. You will find a wide selection of fresh seasonal produce, specialty spreads, jams & jellies, honey, syrups, sauces, and dairy products including local cheeses and butter.

Apple Cider donuts from Milburn Orchards in Cecil County MD

But no trip to Milburn Orchards is complete without a freshly made apple cider donut from the bakery. Grab one for there or take a dozen home.

Dove Valley Winery

If you love wine, you will want to visit Dove Valley Winery (645 Harrington Road, Rising Sun, MD). This family-operated winery is located just outside Rising Sun. The winery produces over a dozen varietals, and they have been winning awards since 2009. Throughout the year they host a number of events including hands-on art workshops, concerts, and theatre.

Wine Grapes in vineyard with blurred background

Attend the Cecil County Fair

The Cecil County Fair (Fair Hill Fairgrounds, 4640 Telegraph Road, Elkton, MD) may be the event of the summer in this rural county. Held the last full week in July, this 4-H fair is everything you would expect of a rural county celebration: Tractor parades, truck and tractor pulls, demolition derbies, a rodeo, livestock competition, and, of course, the Midway.

Kids of all ages can choose from classic carnival rides including the Zipper, the Himalayan, the Swings, and the Ferris Wheel. The youngsters will thrill at the prospect of riding the carousel, the little boat ride, and the giant slide.

Cecil County Fair night shot

And who can refuse the temptation of good ol’ country carny food? The smell of sausage sandwiches, hotdogs, and funnel cake hangs in the warm summer air. But the vendors selling ice-cold lemonade, slushies, and water ice are always among the favorites.

The teenage girls show up to see and be seen. Dressed in shorts and cowgirl boots they play the part. And the carnival barker urges the teenage boys to win something for his gal. 

Rodeo at the cecil County Fair

For the older men whose pedigrees run deep in the farming community, the Detroit Shootout Classic Tractor Pull is the reason for the season. It’s been said that this competition draws people from many miles around.

Horsing Around at Fair Hill

Cecil County and more specifically Fair Hill Natural Resource Center has become a leading destination for horse events and horseback riding in Maryland. Fair Hill International events include the Fox Catcher Endurance Ride, USEA/USEF Recognized Horse Trials, DerbyCross (a combination of cross country and show jumping, rolled into one course), and the Elk Creek Driving Event.

Fair Hill International Maryland 5-Star

But the premier event is the Maryland 5-Star, previously known as the Fair Hill International, one of only two 5-Star events in the United States, and seventh worldwide. Known as the triathlon of equestrian events this multi-day competition features dressage, cross-country, and show jumping.

Terrific Restaurants nearby

Elkton and Cecil County have some fantastic places to dine. Allow me to tell you about some of my favorites. Most of these make the list because they are in amazing settings and offer scrumptious food.

Crabcakes and salad


If you’re a crab-lover you won’t want to miss Woody’s (29 South Main St., North East) in the town of North East. This is a traditional crab house. The kind where tables are covered in paper and you pick (clean) your own crabs. Although, generally, if I’m picking my own crabs, I don’t do it at a restaurant. This is an hours-long affair for me.

However, I do enjoy the other items on Woody’s menu. My favorite is their crab cakes. Get them as part of a sandwich or as an entrée. Either way, you won’t be disappointed. I also recommend starting with either the Crab Bisque or Crab Soup. Both are yummy.

Maryland Crabs

Unwined on the Water at Triton Marina

Unwined on the Water ( 285 Plum Point Rd., Elkton) is located at Triton Marina situated on the Elk River, a major tributary feeding the Upper Chesapeake Bay, Unwined offers outdoor seating and an indoor bar.  Frequently they have live music and if you are so inclined, start a volleyball game or a round of Cornhole.

The menu offers a wide selection from finger foods to full-blown meals like the Mediterranean Steak, a marinated ribeye topped with a tapenade of olives, tomatoes, and feta cheese drizzled in a balsamic reduction. I can’t think of a better spot to relax and Unwined!

Triton Bar and Grill Smokehouse Burger

Lee’s Landing

Situated on the Susquehanna River in the quaint historic town of Port Deposit Lee’s Landing (600 Rowland Drive, Port Deposit) offer live bands on most days throughout the summer and a festive atmosphere on the weekend.

The menu offers appetizers, a variety of sandwiches, wraps, and tacos as well as steamers and pizza. If you go, I highly recommend the Roasted Brussel Sprouts and the Shrimp and Crab Mac and Cheese. These are both appetizers but if you order both you will have more than enough for a meal. I’ve heard great things about their Fish Tacos too.

Lee's Landing Port Deposit at sunset

Old South Smoke House

If you love BBQ then you must try Old South Smoke House (1195 Jacob Tome Highway, Port Deposit). Just a few years ago this was a little tiny roadside place. But it has certainly been discovered. That’s because this place is crazy good!

Whether it’s brisket, pulled pork, chicken, or ribs that you desire, Old South Smoke House is sure to please. Oh, and if you can’t decide then you will want to order the Ultimate BBQ. This way you won’t have to choose. Dinners are served with a side and a “hunk” of cornbread. Portion sizes are huge. But you will want to leave room for dessert.

Ultimate BBQ at Old South Smoke House, Port Deposit MD

Schaefer’s Canal House

Enjoy lunch overlooking the canal and in the shadow of the Chesapeake City Bridge. Schaefer’s Canal House (208 Bank St., Chesapeake City, MD) is located on the north side of the canal and at the termination of the Mike Castle Trail aka the C and D Canal Trail.

The restaurant offers casual waterfront dining with both indoor and outdoor seating. The menu consists of appetizers, burgers, tacos, and pasta as well as full entrees. As you might imagine the menu is seafood heavy but you will also find beef and chicken options as well as vegan and gluten-free selections.

Schaefer's Canal House

Chesapeake Inn

Sit on the deck and enjoy a casual meal and live entertainment or head to the main dining room for a more formal setting or just to escape the heat on a hot day. Either way, you will have a spectacular view of the marina and the C and D Canal.

The Chesapeake Inn (605 2nd Street, Chesapeake City, MD) offers lunch and dinner as well as Sunday Brunch. The deck has its own menu including appetizers, brick oven pizza, tacos, pasta, and more.

Chesapeake Inn

For Sunday brunch, my husband is a fan of their Eggs Benedict while I usually go for the Chesapeake Benedict which is a variation on the classic topped with lump crab meat. The Chesapeake Inn is a popular spot for special occasions and wedding receptions.

There is a private marina for docking. And here’s a little secret: If you arrive at the Chesapeake Inn by JetSki or dinghy there is free docking available. WooHoo!

Backfin Blues

If you are looking for an amazing steak, this is your place. Located in Port Deposit, Backfin Blues (19 South Main St., Port Deposit, MD) might have the best steaks I’ve ever had. And if not the best ever, it was certainly the finest I’d had in a very long time. In addition to an outstanding meal, we received top-notch service. With cloth table linens and exceptional food, this is the perfect spot for date night.

Amazing Filet at Backfin Blues in Port Deposit MD

Accommodations in Elkton

Elk Forge B and B

If you are looking to get away from lackluster chain hotels, Elk Forge Bed and Breakfast (807 Elk Mills Road, Elkton, MD) is far from ordinary. This is a lovely property with 14 suites and 2 apartments with each unit uniquely decorated. All units have their own bathroom and most have a whirlpool tub and fireplace.

Elk Forge Entrance

This charming inn sits on a beautiful 5-acre piece of land that backs onto the Fair Hill Nature Reserve. Walking trails can be accessed from the property.

After a day of hiking get your tired muscles massaged at the on-site Tea Garden Spa. The spa is a full-service spa offering massages, facials, wraps, and more. Packages are available.

Elk Forge Suite

Fairwinds Farm and Stables

Equestrian lovers looking for the perfect place to stay need to look no further than Fairwinds Farm and Stables (41 Tailwinds Lane North East, MD). This BnB is situated on a 52-acre working horse farm that provides the true country BnB experience. The hosts, Joann and Ted are both lovely and go out of their way to make you feel at home.

The inn is a charming restored Victorian-era home. The owners have done a very nice job marrying the convenience of modern amenities with original fitting creating a comfortable environment.

Room at Fairwinds farm and Stables

Those wishing to take a lesson or go for a trail ride are in luck.  The farm features both an indoor and an outdoor riding ring. And you will find acres of trails to ride just out the back door.

If you happen to be traveling with your horse you will find 12X12 stalls for their equine traveling companions. Straw bedding, feed, and hay are all provided. 

Whether you are on the road with your horse or not, you should take some time to explore the property and meet the animals. Check out the gardens, take in the fresh air from the porch, or head to the pond to cast a fishing line.

Next time you are passing through the area on I-95 I hope you will give Elkton, Cecil County, and the Upper Chesapeake, a try. Better yet plan a weekend getaway that blends the best of rural and bay life. With tons of history, outdoor activities, quaint towns to explore, and more, I think you may be pleasantly surprised at all this area has to offer.

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24 Responses

  1. This sounds like the perfect Sunday for me and my pooch! With hikes , horse back rides, kayaking, and an endless amount of things to see and do. I’ll have to refer to this article when I visit Chesapeake.

  2. I love the outdoors and this area looks perfect for dogs. With it being so close to the water, the seafood must be so fresh. I definitely would check out the fish tacos.

  3. This is a part of the eastern US we have not yet visited. So we will need to plan a visit to the Upper Chesapeake Bay Area. Lots of outdoor areas for hiking is a definite draw. Although I would definitely want my bike for the 17 mile C and D Canal Trail. Wine and ice cream would be the bonus for all that outdoor exercise.

  4. I love that you focused on pet friendly things! It\’s always such a struggle to find somewhere that\’s pet-friendly to stay at unless you go camping which I don\’t like doing.

  5. What a great idea to include information in this guide about how to travel with a dog. While I don\’t personally own a pet, many of my friends and family do and its a constant struggle to find information about what places welcome their furry friends.

    1. I do think it is getting easier to travel with pets. More of the chain hotels are starting to realize that some people wouldn\’t dream of going away without their pooch. If they don\’t offer it, the pet owner will find someplace that does.

  6. What a great article! We are always into pet friendly places to visit! Wine, water, and trails are always on the list! We would love to visit Maryland in the near future.

  7. Sounds like some great adventure with the pup! We need to bring ours along more often somehow! (It\’s hard with a full van of four young kids!) It\’s great there are so many dog-friendly options!

  8. I\’ve been in Maryland for ten years now, and I\’ve actually yet to explore Cecil County. It looks amazing and I love that you can take your furry friends! Looking forward to putting this on my list of local to-dos.

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