OLD BRIDGE

Teddi
OLD BRIDGE

Food scene

Fun, Elvis-themed breakfast and lunch place. One of the few in Chestertown which serves breakfast.
Beverly's Family Restaurant
11 Washington Avenue
Fun, Elvis-themed breakfast and lunch place. One of the few in Chestertown which serves breakfast.
Nice, dressy dinner restaurant.
13 locals recommend
Watershed Chestertown
337 High Street
13 locals recommend
Nice, dressy dinner restaurant.
American Food, lunch and dinner.
14 locals recommend
Uncle Charlie's Bistro
834 High St
14 locals recommend
American Food, lunch and dinner.
Delicious Japanese food served in a hip atmosphere in an old mill. Nice historic setting. They also have a few Thai dishes.
49 locals recommend
Cafe Sado
205 Tackle Cir
49 locals recommend
Delicious Japanese food served in a hip atmosphere in an old mill. Nice historic setting. They also have a few Thai dishes.
Great southern barbecue with all the sides to compliment. Fantasticfood cooked and served by the sweetest people!
7 locals recommend
Phat Daddy’s BBQ Shack
205 Spring Avenue
7 locals recommend
Great southern barbecue with all the sides to compliment. Fantasticfood cooked and served by the sweetest people!
Funky little Breakfast sandwich lunch items place. It's a place people meet to chat and sip!
25 locals recommend
Play It Again Sam
108 S Cross St
25 locals recommend
Funky little Breakfast sandwich lunch items place. It's a place people meet to chat and sip!
Real Italian food right in Chestertown. The place is nicely appointed, good atmosphere and bar. The bread is addictive!
27 locals recommend
Luisa's Cucina Italiana
849 Washington Ave
27 locals recommend
Real Italian food right in Chestertown. The place is nicely appointed, good atmosphere and bar. The bread is addictive!
"Procs" as the locals call it has the best pizza in town plus other italian specialties including pasta. They make a great Greek salad too. VERY casual!
15 locals recommend
Procolino's Pizza
711 Washington Ave
15 locals recommend
"Procs" as the locals call it has the best pizza in town plus other italian specialties including pasta. They make a great Greek salad too. VERY casual!
Quint place for wine, cheese and tapas.
13 locals recommend
Casa Carmen Wines
312 Cannon St
13 locals recommend
Quint place for wine, cheese and tapas.
Charming and renovated to look like the soda fountain it originally was in the 19 th century. They serve breakfast sandwiches, lunch and more importantly, homemade ice cream.
8 locals recommend
Stam's Luncheonette
215 High Street
8 locals recommend
Charming and renovated to look like the soda fountain it originally was in the 19 th century. They serve breakfast sandwiches, lunch and more importantly, homemade ice cream.
Great place for some unique beers, but not known for its food.
13 locals recommend
BAD Alfred's Distilling
323 High St
13 locals recommend
Great place for some unique beers, but not known for its food.
Home baked bread and pastries. Sandwiches and more.
37 locals recommend
Evergrain Bread Company
201 High St
37 locals recommend
Home baked bread and pastries. Sandwiches and more.
Excellent selection of wine and cheese. Top rated for their customer service.
22 locals recommend
Chester River Wine & Cheese Co.
117 S Cross St
22 locals recommend
Excellent selection of wine and cheese. Top rated for their customer service.
Nice American fare. some nice seafood and local favorites.
23 locals recommend
Fish Whistle
100 George Street
23 locals recommend
Nice American fare. some nice seafood and local favorites.
Lovely American food in a beautiful historic house. Eat outdoors by the water or enjoy the dining room or bar.
14 locals recommend
Kitty Knight
14028 Augustine Herman Hwy
14 locals recommend
Lovely American food in a beautiful historic house. Eat outdoors by the water or enjoy the dining room or bar.
Caters to the gluten-free folks, but even if you eat gluten, food is worth enjoying!
10 locals recommend
Figg's Ordinary
207 S Cross St
10 locals recommend
Caters to the gluten-free folks, but even if you eat gluten, food is worth enjoying!

Arts, Entertainment, Shopping and More

I can't even begin to list all the places you will have fun visiting, but walk around downtown Chestertown and poke into each place to see what is going on! The first Friday evening of each month features "First Friday" activities and the shopkeepers are open and you may find music and food being promoted outdoors and indoors.
This is a pleasant place to visit if you love felines! It's basically what would be referred to as a "cat cafe" in other places. No food or beverages are served, but you can visit with the most charming cats. They are adorable and entertaining. the place is kept meticulously clean. Advance reservations are strongly recommended.
Cat Colloquium
215 High St
This is a pleasant place to visit if you love felines! It's basically what would be referred to as a "cat cafe" in other places. No food or beverages are served, but you can visit with the most charming cats. They are adorable and entertaining. the place is kept meticulously clean. Advance reservations are strongly recommended.
Fine art gallery that has ever-changing pieces by various artists.
Les Poissons Gallery
206 South Cross Street
Fine art gallery that has ever-changing pieces by various artists.
Art gallery with revolving exhibits.
9 locals recommend
MassoniArt Gallery
203 High St
9 locals recommend
Art gallery with revolving exhibits.
Constantly-changing exhibition.
Artists' Gallery
239 High Street
Constantly-changing exhibition.
Every Saturday 8:00 a.m. to noon. Go to Fountain Park in the center of town. All kinds of artisan creations. A great place to shop for locally made gifts, baked goods, produce and more!
14 locals recommend
Marylands Chestertown Farmers & Artisans Market
118 North Cross Street
14 locals recommend
Every Saturday 8:00 a.m. to noon. Go to Fountain Park in the center of town. All kinds of artisan creations. A great place to shop for locally made gifts, baked goods, produce and more!
Historic theatre which features a variety of plays and shows often featuring local actors.
13 locals recommend
Garfield Center for the Arts at the Prince Theatre
210 High St
13 locals recommend
Historic theatre which features a variety of plays and shows often featuring local actors.
Directly across the street from the Old Bridge house. Delightful things for home and clothing. There are so many lovely items for gifts, including unique items for little ones. this is my favorite place to shop in all of Chestertown! I always find a treasure here.
Bohemia Trading Company
7400 Church Hill Rd
Directly across the street from the Old Bridge house. Delightful things for home and clothing. There are so many lovely items for gifts, including unique items for little ones. this is my favorite place to shop in all of Chestertown! I always find a treasure here.

Traveler advice

Book before you go

Museums and attractions

Many things to do in Chestertown fill up fast, so if you want to visit these places, try to reserve before your trip.
Traveling with kids

Baby Equipment

The OLD BRIDGE house offers you the following baby equipment which is washed and sanitized after guests use it. Pack-N-Play with mattress, mattress cover, sheets and light blankets. High Chair Stroller
Don't miss

Stop at the Visitors Center in Chestertown

The visitors center will give you more direction and ideas on what to do based on your interests. https://townofchestertown.com/visitors-3/