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With slogans like, “The pace is different here” and “You belong here,” you know you’re entering an extraordinary place in Caroline County, Maryland. With less than 5,000 people, you can feel a sense of community as soon as you enter Denton. So while planning your Eastern Shore itinerary, you may have wondered whether you should stop in Denton. Here, we share the 15 best things to do in Denton, Maryland!
First things first, stop at the Wharves of Choptank Visitor Center for visitor guides and information. The Center can give you maps and the most up-to-date information on what is open and the best times to visit. Check out our advice on what to do in Denton, Maryland:
Best Things to Do in Denton, MD
1. Stroll the streets of downtown Denton.
Park your car in the town lot on N. 3rd Street between Market and Gay Streets. You’ll be perfectly placed to walk to most of the main attractions in downtown Denton.
Lined with small shops and other local businesses, Market Street’s approximately eight-block area comprising the downtown holds unexpected treasures. The friendly greetings make it easy to see that locals love their town and are happy to welcome visitors.
A perfect example of the pride residents take in their town is the Denton in Bloom project. Businesses and families can sponsor flower baskets along Market Street, adding to the city’s curb appeal.
2. Attend a Friday Night Cruise-In.
The second Friday of every month, from May to October, is an opportunity to see and be seen in your collectible automobile. This family-friendly event is held along Market Street. Admire some great cars at the Friday Night Cruise-In!
3. Show off your cornhole skills.
Held on the third Thursday of every month from May to October, a $5 registration fee is all that separates you from some friendly competition. Market Street becomes pedestrian friendly as the best cornhole players vie to take home the cornhole trophy!
Purchase Night Kitchen Coffee at various places around town, including the adjacent Craft Bakery & Cafe.
4. Learn about nature at the Adkins Arboretum.
Nature lovers, and those learning to love nature, will adore the Adkins Arboretum. As visitors walk over the bridge connecting the parking lot to the visitors’ center, the sounds of residents greet them – the real locals! Frogs, birds, and the occasional flipping fish make their presence known.
Guests explore five miles of paths, whether on a self-guided tour, using the audio guide, or even on a guided tour (available on the first Saturday – by reservation only!). The Arboretum features a variety of environments; from prairie fields to wetlands, there’s a little bit of everything.
One of the best things to do is sit at one of several red chairs along several trails and just listen. Enjoy the quiet, disturbed only by the sounds of the surrounding nature. This is why it is one of the best things to do in Denton, Maryland.
5. Bike or hike the trails at the Tuckahoe State Park.
Surrounding the Adkins Arboretum is the Tuckahoe State Park, featuring 20 miles of hiking, biking, and equestrian trails. The trails of both connect so visitors can explore further distances if they wish.
You can even participate in the Tuckahoe Triathlon, hosted annually in June.
6. Learn about quilting at FACES.
Denton is home to the Fiber Arts Center on the Eastern Shore (FACES), a unique institution encouraging all fiber arts. From holding exhibitions to teaching classes on different fiber arts, FACES has leaped to the forefront as a leader in promoting the fiber arts.
It’s a fun stop to learn about a relatively unique form of art.
Connected to FACES and the preservation of history are the quilt blocks on the sides of historic buildings throughout the Eastern Shore. The Byway Quilt Block Trail features hand-painted replicas of quilt blocks along the Harriett Tubman Underground Railway Byway.
7. Follow the Harriett Tubman Underground Railway Byway.
Learn the history of Harriett Tubman through this self-guided tour stretching 125 miles through areas of Maryland and Delaware before ending in Philadelphia. The Byway is the only place where you can learn about Harriett Tubman’s birth, life, and where she fled from.
You can even schedule a tour at the Harriett Tubman Byway Visitor Center in nearby Cambridge.
8. Admire art at the Caroline County Council of Arts (CCCA).
Art lovers will appreciate everything the Caroline County Council of Arts offers. Encouraging local artists to display and showcase their talents, CCCA also sells products made by them. A rotating artist of the month gets to show their works along the many walls of the building at The Foundry. You can’t miss the building with its two wire statues out front!
The CCCA is all about the community by offering art classes and opportunities for local artists and supporting The Foundry and FACES.
When the town created its pennant flags to display along Market Street, it allowed 12 main artists to make the main design. But then it opened the opportunity for all locals to create their designs – and people of all ages obliged! You can find local designs on the back of each pennant.
9. Attend one of its many festivals
There’s nothing better than a festival in a small town as a way to celebrate the outdoors, arts, and entertainment. Denton hosts its festival known as the Caroline Summerfest. The streets around Caroline County Courthouse close so people can safely explore vendors and food stalls and listen to great music without having to avoid traffic. The celebration lasts all weekend, and a river run race is held on the Choptank on Saturday. The festivities are capped off with a fireworks display. Great fun is had by all at the Caroline Summerfest!
One unique event held downtown Denton is the Supper at Sunset. Guests need reservations to enjoy an evening of alfresco dining supporting the local community. The effort is led by Chef David and a local winery, pairing a four-course meal with superb local wines.
This popular event is held annually in September.
10. Enjoy freshly baked goods at Craft Bakery & Cafe.
What do you get when you combine a baker, a beautiful downtown location, and a desire to make everyone feel welcome and loved through food? You get the birth of a local eatery. Open for breakfast and lunch, Craft Bakery & Cafe bakes all of their stuff fresh in-house with products from local producers.
It’s a great place to take a break from your downtown exploration with a fresh cup of coffee or iced tea (they had peach when I visited!) and to fill your belly with a delicious pastry or sandwich. Tastes even better than homemade!
11. Try freshly roasted coffee from Night Kitchen Coffee.
With the motto, “Life is too short to have bad coffee,” you know you’re in for a treat when you sample delicious Night Kitchen Coffee. This small-batch coffee roaster uses in-house seasonings made with high-quality ingredients to promote sustainable and high-quality coffee farmers.
12. Sail the Choptank River
Book a tour with River City Cruise Company on a pontoon boat where you can schedule a historical tour, wildlife spotting, or even a sightseeing tour. It’s a great way to see Denton from a different point of view. Check them out on Facebook.
13. Check out the Museum of Rural Life.
As one of only a handful of American counties that survived only on agriculture for over 300 years, the museum preserves the unique history of this county. The Museum of Rural Life is the place to learn all about what it was like (and still is in many ways, to live in rural areas of the Eastern Shore. Visitors can see portions of four historic homes that have been preserved. Sadly, the museum is only open on Saturdays, so plan accordingly.
14. Shop at the Farmers Market.
Unlike other destinations where you need a Saturday morning to visit the Farmers’ Market, Denton holds theirs on Wednesday evenings from 4:30 – 6:00 pm from March through September.
This is your opportunity to purchase something from the local vendors as a souvenir or shop for gifts with a local touch. You’ll find the Farmers Market at the corner of Market and N. 3rd Streets.
15. Take a ghost tour of Denton
Fans of the dark and mysterious will enjoy taking a ghost tour in Denton. Denton has a reputation as one of the most actively haunted towns along the Eastern Shore. The most haunted location is the Denton Jail. Book a ghost tour to add to your Eastern Shore education.
Know Before You Go to Denton MD
Where is Denton, MD?
Denton, Maryland, is located in Caroline County on the Eastern Shore of the Chesapeake Bay. Located on the shores of the Choptank River, farm fields surround Denton.
When is the best time to visit Denton, MD?
The weather in Denton is best in May and June and again in September. The town gets hot and muggy in the summer (like most of the Eastern Shore!). Denton is the coldest in January and February.
Where to stay in Denton, MD?
There are a few options for places to stay in Denton. Here are some nearby options:
The Tidewater Inn: Restored and beloved and a hit with bridal parties, The Tidewater Inn features modern rooms with all the amenities you would want. This is where I stayed, and I can personally recommend it!
Rates during the summer and on the weekends tend to be higher. If you’re trying to get the best bang for your buck, try to visit during the Spring or Fall and during the week.
Booking.comFinal Thoughts on the Best Things to Do in Denton, Maryland
Denton, Maryland, is a cute stop along your Eastern Shore itineraryDenton hits the spot if you’re craving a taste of small-town living! As advertised, the pace of living here is slower, so you can just relax and detox. There’s a reason that the town touts itself as a place where everyone belongs. Plus, the art scene is fantastic! You won’t be sorry you stopped by!
Check out these other Eastern Shore posts:
- Best Maryland Lavender Fields to Visit
- Best Maryland Sunflower Fields to Visit
- 15 Amazing Things to Do in Salisbury, MD
Happy travels,
Annick, The Common Traveler
Raised as a third culture kid living in South America and Europe, Annick caught the travel bug early. As an empty-nester, Annick enjoys sharing her tips for traveling for those with champagne taste and beer budgets.