Obscure Things to Do in Denton MD: and Greater Caroline County

WHY GO: Things to do in Denton MD and the surrounding Caroline County can get rather obscure. But for foodie romantics hunting for an under the radar getaway, this one certainly fits the bill!

To begin, the Harriet Tubman story continues into Denton and Caroline County Maryland. Though a powerful draw, that’s not the only reason to come and stay a few days. There are some surprisingly sophisticated restaurants, funky and cool local-arts and craft stores, and a Specialty High School for the Culinary Arts in tiny Eastern Shore towns surrounded by vast tracks of farmland.

Where is Denton and Caroline County MD? In the center of the Delmarva Peninsula, it’s the premier agricultural county in Maryland, known more for what it grows in the earth than what it gleans from the Bay. You’ll want to stay at least a night. Read on.

The Harriet Tubman saga began in nearby in Dorchester County MD – the place of her birth. So, if you wish, begin you getaway in Cambridge MD. 

Need more Maryland trip ideas? Check out our Romantic Getaways in MD post.

Things to Do in in Denton MD and Surrounding Caroline County

Linchester Mill sign, Preston MD

VISIT: Linchester Mill, Preston

The Linchester Mill complex includes the grist mill, of course, but also Maryland’s only Braille Nature Trail. The mill itself was an inadvertent gathering place for slaves, free blacks, and white sympathizers, who all brought their grain to be milled here.

In fact, though there is no documentation, it’s probable that Harriet Tubman’s father, Ben Ross, came to this flour mill. He lived just two miles away in Poplar Neck, the spot from which he, his wife, and Harriet escaped the Eastern Shore. The Mill, currently in a ramshackle state, is open for self-guided tours.

You’ll get a good sense of how dense the woods were in the mid 1800’s along Hunting Creek. Tubman and her family and friends had to find their way along the creek that feeds into the Choptank River in the dark of night. It was a punishing journey.

Hidey Hole, Webb House, MD

STOP: James Webb Cabin, Preston, on Tubman Byway

Owned by free Black farmer, James Webb, this 1850’s homestead was a typical African American one-room farmhouse with loft and root cellar. Harriet Tubman’s father and mother, Ben and Rit Ross, probably lived in a very similar structure at nearby Poplar Neck. There is no documentation that that “potato hole” was a hiding place for freedom seekers. But that doesn’t mean it wasn’t.

Steamboat Wharf, Denton MD

VISIT: Denton Mercantile at Steamboat Wharf, Denton

The Denton Mercantile at Steamboat Wharf doubles as an Underground RR Byway stop. Situated on the Choptank River, slaves were offloaded for auction at Steamboat Wharf. Ironically, the Wharf also teemed with free Black watermen who brought news, passed gossip, and whispered escape advice.

One such celebrated escapee was Moses Viney, whose portrait hangs in the Union College library in Schenectady NY. One Easter Sunday, Viney fashioned oars from two fence posts and rowed a stolen canoe to freedom.

Viney planned his getaway for months, training the slave-catcher’s hounds to quietly expect treats and then go home, rather than loudly give chase. He reached Schenectady, worked for Union College, and owned his own carriage service. After awhile, Viney saved enough to purchase some downtown buildings.

You’ll most likely learn about Viney on a River Run Cruise (operating adjacent to Steamboat Wharf), that offers Historical, Wildlife, and Siteseeing tours on the Choptank River.

Escape from Poplar Neck, Museum of Rural Life, Denton MD

VISIT: Museum of Rural Life, Denton

Plan to spend 20 minutes or half an hour in this 1819 Town Home, now the small Museum of Rural Life. Take a long look at the original “Escape From Poplar Neck” – the painting of Harriet Tubman and her parents riding for their lives out of Maryland. (A copy hangs in the Harriet Tubman Visitor’s Center in Cambridge).

Inside Cabin, Museum of Rural Life, Denton MD

Also find an original farm cabin and a parlor from a 1790 home. The photomural titled the “Seeding of Alaska Peas,” dated March 1906, allows a glimpse of local farm life. No big surprise that at one point, Caroline County MD was considered the “Garden of America.”

The Foundry, Local Arts and Crafts, Denton MD

SHOP: Foundry Art Gallery and Gift Shop, Denton

Forward thinkers in this tiny farm town took a derelict neighborhood and turned it into an “Arts and Entertainment” district.  These artsy forward thinkers evolved into the Caroline County Council for the Arts (CCCA), which offered artists incentives to buy or rent houses, fix them up and use them as studio/shops. The results have been fantastic – for creatives, visitors, and locals alike. A true win-win-win.

Jewelry at The Foundry, Denton MD

The Foundry Art Gallery gathers the work of 40 local artists in one place, with offerings as far from cookie-cutter as you can get. You’ll find arts and crafts here you won’t see anywhere else for much less than you’d spend in cities or resort towns.

SHOP: Other shops on 4th in Denton

Fiber Arts Center  hosts “sit and sew” groups.

Bargain Beverage, Denton MD

SHOP: Bargain Beverage

In the know beach-bound tourists stop here between Baltimore and the beaches for booze. It’s apparently the cheapest and most convenient place on the road to stock up on spirits. But now that you know what else is in town, you’ll want to stay awhile.

Adkins Arboretum, MD

HIKE: Adkins Arboretum, Ridgely

With four miles of well-marked bike and walking trails, the 400-acre Adkins Arboretum has been a magnet for nature lovers and birders since it opened in the 1980’s.

Bring your dog (treats and bowls of water provided). Wander the wetlands, woods, meadows, streams and gardens. Investigate native Maryland plantings. And say hi to four resident goats that eat invasive species – a low-tech approach to a significant problem.

If you have an hour, or haven’t been here in awhile, stop in to the small but informative Visitor’s Center. Alternately, check out this webpage, Nature’s Role in the Underground Railroad,” a realistic imagining of what it felt like to be lost in the woods in the dark, with audio accounts of stops you can take along the way.

This tangled landscape hasn’t changed much since Harriet Tubman’s time, when she and others faced grueling natural obstacles “while breaking from bondage.”

Sporting Clay, Schrader's Outdoor, Denton MD

DO: Shoot Clays at Schrader’s Outdoors, Henderson (aka Schrader’s Bridgetown Manor)

Schrader’s Bridgetown Manor is known as a “hunting lodge” and sportsman’s retreat. In fact, there’s a hidden poker room behind a wall, and lockers for muddy camouflage-wear and ammo. But Schrader’s also offers one of the best Sporting Clay courses – what aficionados call “golf with a gun”- in Maryland.

You’ll find 16 stands on a scenic one-mile course, taking you through forest, field and by a turquoise-water-filled gravel pit. For those who want to test their sharp-shooting skills but don’t want to kill anything, Sporting Clay is the perfect activity.

Come for the day, or plan to stay the night in one of 10 guest rooms. Schrader’s Outdoors runs many competitions and programs, including deer, small game, turkey and upland bird hunting, 3-D archery, sport fishing, Corporate Team Building, and other packages on 25,000 acres of “the finest hunting properties on Maryland’s Eastern Shore.”

Check website rates, dates, and hours.

Restaurants in Caroline County MD

Market St. Public House, Denton MD

EAT/DRINK: Market Street Public House, Denton

Raise a glass of expertly poured Guinness in the “Cheers” of Denton MD, Market Street Public House.  The food is decent and the vibe celebratory. It’s a gathering spot and local watering hole, where everybody knows your name. Subsequently, it’s packed nightly and loved by all.

EAT: Caroline’s In Denton

Caroline’s in Denton has been ascendant since it first opened in the early 2020’s. A true farm-to-table restaurant (how could it not be – surrounded as it is by farmland), reaching out to the Chesapeake Bay, signature dishes range from Classic Oyster Stew, Jumbo Lump Crab Cakes, Butternut Squash Bisque, and Cider Brined Pork Chops. All showcasing the chef’s skills, many patrons return weekly for what they consider one of the best restaurants in Caroline County.

Caroline Culinary Arts Center, Denton MD

EAT/LUNCH: Shore Gourmet Market at Caroline Culinary Arts Center

Here’s a not so hidden secret in Denton. You can get a great breakfast, lunch, picnic meal, and “Wednesday Dinner” in the gleaming, renovated culinary center’s café.  Shore Gourmet Market at Caroline Culinary Arts is a local take-out treasure connected to a feeder school for top restaurant staff.

I didn’t expect this caliber of fresh and creative at a specialty trade High School. But hot pressed sandwiches and the like impressed me no end. Buy breads, bagels, salads, hot sandwiches, and other prepared food to eat in or take out. And then, check out the spotless instructional kitchens on the main floor and upstairs. You might just meet a “Top Chef” in the making!

EAT/VEGAN: Earth Tones Cafe

Little Denton MD is so ahead of its time, it’s got a plant-based restaurant not specifically for vegans: the cute, contemporary Earth Tones Cafe. Get your toasts, bowls, and um, alcoholic beverages (cocktails, beer and wine) here. Being vegan is healthy, but doesn’t have to be stuffy!

Where to Stay in Caroline County

Turnbridge Manor Room Denton MD

STAY/REUNION: Turnbridge Manor

Formerly a B&B, Turnbridge can now be rented out as a whole house on Airbnb or VRBO – or other rental sites. The cost (in Jan. ’24) is $500 per night, whether or not you’d like to hole up in one guest room or invite friends and take up all five. You get the run of the house, a cook’s kitchen, and access to great restaurants and attractions in Denton MD – just a short walk away. An incredible deal.

STAY: Best Western Denton Inn

If you’d like a traditional, full service hotel, the Best Western Denton Inn is a good choice for those who’d like an nice, clean room in Denton.

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  • Malerie Yolen-Cohen

    Malerie Yolen-Cohen is the Author of the cross-country travel guide, Stay On Route 6; Your Guide to All 3562 Miles of Transcontinental Route 6. She contributes frequently to Newsday, with credits in National Geographic Traveler, Ladies Home Journal, Yankee Magazine, Shape.com, Sierra Magazine, Porthole, Paddler, New England Boating, Huffington Post, and dozens of other publications. Malerie’s focus and specialty is Northeastern US, and she is constantly amazed by the caliber of restaurants and lodging in the unlikeliest places.

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