We may earn money or products from the companies mentioned in this post.
Looking for a new way to explore Maryland’s Eastern Shore? Skip the beach and discover charming inland towns. One such beautiful destination is Talbot County’s “big city” of Easton, with a population of about 11,000. Easton has won accolades as both one of America’s Best Small Towns and one of the top 100 Small Art Communities. There are so many things to do in Easton MD involving art!
Easton is popular with those in the know – including those who know this little town hides charming treasures. Here are all the best things to do in Easton, Maryland!
Best Things to Do in Easton, Maryland
1. Take a historical walking tour of Downtown Easton.
Held on the third Saturday of the month in April through December, the Talbot Historical Society offers two tours. The first tour describes the historical buildings of downtown Easton as you walk by them. The second tour, held at noon, focuses on Easton’s architecture.
Considering that the then village was officially founded in 1710 around the important courthouse, Easton has witnessed many historical events. Visitors will learn about the American Revolution when Easton prepared itself to ward off the British. Since the buildings can’t talk – the historical volunteers fill in the details!
2. Get a little scared on a ghost tour.
In under two hours, you and your group will be regaled with tales of ghosts and Easton’s sordid past. Bring your walking shoes and an umbrella, as the tours are not canceled due to the weather. While standing outside each location, a storyteller from Chesapeake Ghost Tours will fill you in on the intriguing and scandalous events that have occurred over the centuries. It’s a unique way of learning about Easton!
3. See the plein air movement up close.
Easton hosts the country’s largest and most prestigious plein air festival annually in July. This juried competition features artists who apply to participate in the Plein Air Easton Art Festival. Fifty-eight artists spend the week in Talbot County painting at their favorite locations. Easton visitors during this time will enjoy seeing these artists working their craft in public spaces.
4. Explore the historic gardens.
Directly across the street from the Tidewater Inn, behind the historic James Neall House, visitors can find the beautiful federalist gardens. Maintained through a partnership with the Talbot County Garden Club, the Talbot Historical Society Gardens contain a shade garden, perennial beds, and an herb garden, among others. The Gardens are open to the public every day during daylight hours. This location is a favorite with the artists at the Plein Air Easton Art Festival.
5. Discover new artists on the Art Walk.
Held on the first Friday of every month, the Easton Art Walk allows local artists and galleries to showcase their work and for visitors to discover new artists. Because more people are exploring the shops during this time, if you are naturally intimidated entering art galleries, you’ll find yourself more at ease exploring them. You may even have an opportunity to meet the artist who created a piece of art that interests you.
6. Shop the stores downtown Easton.
Walk along tree-lined East Dover and Goldsborough Street, and their intersecting streets, to find cute little shops and businesses, like La De Da (women’s clothing) and Justamere Trading Post (tea shop with unique jewelry and gifts), to mention just a few. Whether you’re looking for clothing boutiques, vintage bookstores, or hunting for an antique to add to your collection, you’re sure to find something along the streets near the Tidewater Inn.
7. Enjoy a farm-to-table meal at Out of the Fire.
Easton is no slouch when it comes to gourmet cuisine. You’ll be surprised at how many outstanding food options you have to choose from! If you want to eat well while doing good, then check out Out of the Fire.
The powerhouse behind Out of the Fire is the owner, Amy Haines, who has pushed to give the restaurant a community focus. The menu sources the freshest local products, so the menu is constantly changing. The waitstaff will happily recommend the best the restaurant offers daily.
With a motto of: Eat Well. Be Well. Give Back, Out of the Fire, instills a sense of community, even for guests. Local artists’ artwork hangs on the walls of the restaurant and is available for purchase.
8. Practice your swing on the golf course.
The aesthetically Eastern Shore-designed 18-hole championship and 9-hole executive golf courses at Hog Neck Golf Course are among the top 25 public golf courses in the country. Dust off your clubs and bring them along for an outstanding challenge, no matter your handicap!
9. Catch a show at the Avalon Theater
If you’re looking for a live music show or a theater piece, do yourself a favor and book tickets at the Avalon Theater. Lovingly restored by the Avalon Foundation, the 400-seat Avalon Theater shines with its art deco interior. The unparalleled acoustics explain why the Avalon Theater has been such a popular live music venue. A smaller, more intimate venue seating about 60 called the Stoltz Listening Room allows guests to get closer to the artist.
10. Sample the wines at the Far Eastern Shore Winery
This family-owned micro-winery is an unexpected find in Easton. The tasting room is the perfect way for visitors to sample Far Eastern Shore Winery’s offerings by trying a flight (or two!). Fans of sweet wines will especially appreciate their selection and the chocolate raspberry port receives excellent reviews. The staff is friendly and helpful in navigating the choices. Check out their Facebook page for upcoming events and specials.
11. Enjoy the Outdoor Concert Series on Saturday nights.
Produced by the Avalon Theater on Saturday nights is the popular Outdoor Concert Series. During the summer, a few blocks along N. Harrison Street, next to Hunters’ Tavern and the Avalon Theater, close to vehicle traffic so that pedestrians can enjoy live music acts setting up near that intersection. One of the best ways to enjoy this is to book a table at the Tidewater Inn’s Hunters’ Tavern, requesting a patio table. You’ll be able to enjoy the music while watching people walk by.
12. Sip on a tall cool one at 4 Dogs Brewing Co. & Pub.
Craft beer and dog lovers will adore 4 Dogs Brewing Co. & Pub. Serving a variety of styles, all of the beers have dog-themed names, like Last But Not Leashed, St. Beernard, and Easton Terrier. And if you get hungry, try some of their traditional pub fare or Jalapeno Bacon.
13. Create your own foodie walking tour.
With so many delicious places to eat, all within easy walking distance of each other, it is incredibly easy to create your own food walking tour with four to five eateries. Some of the restaurants to consider adding to your list: Legal Assets Craft Food & Spirits, The Wardroom, Out of the Fire (see more above), Sunflowers and Greens, and finish at Storm and Daughter’s Ice Cream.
Places in Talbot County Worth Exploring From Easton
1. Have breakfast at The Galley in St. Michael’s.
This family-owned and operated restaurant offers both traditional and unique breakfast options. Everyone will find something that hits the spot, from crabcakes to buttermilk biscuits, eggs benedict, or any typical breakfast item. Those daring to try something unique should try the Famous Galley Glazer (an egg, cheese, and bacon or sausage sandwich inside a glazed donut) or the Nut So Healthy (a Nutella, bacon, and French Toast panini).
If you’re looking for the best Bloody Mary on the Eastern Shore, you’ll find it at The Galley! It perfectly balances spices and the horseradish bite with the smoothness of tomato juice. If you prefer, Bottomless Mimosas are served every Sunday during brunch. The Galley is also open for lunch if you’re a late riser.
2. Learn about the importance of the Chesapeake Bay at the Maritime Museum.
The Chesapeake Bay Maritime Museum offers a unique way to learn about the regionally significant maritime life of those living and working along the Chesapeake Bay. With a new, expanded welcome center, visitors will learn about different types of vessels and even climb inside a lighthouse to learn what life was like for those who provided this vital service.
In addition to being a museum, they offer an apprentice opportunity for those wishing to learn how to build ships. You can even sign up for day programs to learn specific skills.
New in 2023 is an opportunity to take a 45-minute cruise on one of the floating fleet ships. The museum maintains a dozen ships, dating from 1889 to a 2002 replica, docked at its pier, which visitors can explore up close. The organization is also working on renovating a ship for longer overnight cruises. You’ll need about two hours to see everything if you don’t sail.
3. Explore the town of Oxford.
Another cute little town, Oxford, is just a 15-minute drive from Easton. Established in 1683, it has a population well under 1000, meaning it is beautifully peaceful. One of the best things to do in Oxford is to drive around town looking for the picket fence posts at people’s homes or yards. This fundraiser by the Port of Oxford provides small sections of the unique Oxford fence design for artists to embellish.
You can find a map of all 14 Oxford pickets and a history of this unique fundraiser’s artist, location, and beneficiary. The Oxford pickets remain on display all summer until they’re auctioned at the beginning of September. Check them out!
4. Eat lunch at Doc’s Sunset Grille in Oxford.
Like a beachside crab house, Doc’s Sunset Grille, nestles right up the Trent Avon River and serves a variety of meal options. Choose seafood options, burgers, or bar fare. The crabcake gets high marks. Doc’s is the perfect place to enjoy a meal along the water, watch the sunset, and listen to live music.
5. Ride the Oxford-Bellevue Ferry.
The Oxford Bellevue Ferry connects the Talbot County town of Oxford and the village of Bellevue. The nation’s oldest privately owned ferry service was established in 1683. Each way takes approximately 10 minutes, and guests can exit their cars to look at the towns along the river.
The ferry is open every day during the summer and closes at sunset. In November, the ferry only operates on Saturdays and Sundays. The ferry is closed for the winter from mid-November until it re-opens in mid-April.
Where to Stay in Easton, Maryland
The fabulous Tidewater Inn is the historic cornerstone hotel of Easton. Along with the Tidewater House (their bed and breakfast), it is the premier lodging choice in town. This luxury hotel is the perfect place to unwind during your Easton travels. With 86 newly renovated rooms and suites, you’ll feel like you’re being spoiled during your Tidewater Inn stay.
The rooms are clean and modern, featuring some of the amenities that demanding travelers have come to expect. Several room types include a small refrigerator, sink, and work and sitting areas.
And while brides from Philadelphia, Baltimore, Washington, DC, and Wilmington have long known about the Tidewater Inn as a wedding venue, others are now discovering it too. Who wouldn’t want to stay at a chic hotel with a spa and a cute downtown?
You can find other hotels and two bed and breakfasts if you prefer here.
Final Thoughts on Easton, Maryland
Skip the beach and discover the other towns and villages of Maryland’s Eastern Shore cities with a relaxing weekend in Talbot County’s “big city” of Easton. With its fabulous eateries, cute shops, and walkable historic center, Easton offers something for everyone. You won’t regret a weekend spent in Easton!
Check out these other posts about nearby places:
- 15 Reasons to Add Denton MD to Your Eastern Shore Itinerary
- 15 Fabulous Things to Do in Salisbury MD
- Maryland Sunflower Fields to Visit
- Maryland’s Lavender Fields to Visit
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.