Guidebook for Chestertown
Neighborhoods
Chestertown is an historic small town on the majestic, unspoiled Chester River on Maryland's famous Eastern Shore. It has been since 1782 the home of Washington College. Many shops, restaurants, and bars are within walking distance, and a short drive through the surrounding farmland will take the adventurous traveler to other enjoyable destinations!
31 locals recommend
Chestertown
Chestertown is an historic small town on the majestic, unspoiled Chester River on Maryland's famous Eastern Shore. It has been since 1782 the home of Washington College. Many shops, restaurants, and bars are within walking distance, and a short drive through the surrounding farmland will take the adventurous traveler to other enjoyable destinations!
Historic Sites
Founded in 1782 with a grant from George Washington, this is an historic liberal arts and sciences institution for higher learning.
16 locals recommend
Washington College
300 Washington AveFounded in 1782 with a grant from George Washington, this is an historic liberal arts and sciences institution for higher learning.
Stepne Manor
406 S Cross StGreat for group events like weddings
Sightseeing
Places to visit
Cruise the beautiful Chester River on the River Packet while enjoying good food and drink by Occasions Catering. Book in advance to be assured of a seat!
12 locals recommend
Chester River Packet Company
Cruise the beautiful Chester River on the River Packet while enjoying good food and drink by Occasions Catering. Book in advance to be assured of a seat!
A great place to visit to walk or ride bikes! It's a National Park!
27 locals recommend
Eastern Neck National Wildlife Refuge
1730 Eastern Neck Island RdA great place to visit to walk or ride bikes! It's a National Park!
Wineries and Distilleries
You'll feel like you're in Napa Valley at this beautiful establishment. Jim says the Creme Brulee is the BEST!
26 locals recommend
Chateau Bu-De, LLC Bohemia Manor Farm
237 Bohemia Manor Farm LnYou'll feel like you're in Napa Valley at this beautiful establishment. Jim says the Creme Brulee is the BEST!
Crow Vineyard & Winery
12441 Vansant Corner Rd
Broken Spoke Winery
942 Glebe RdFood and Drink scene
There are really good places to eat and drink in Chestertown, and 15 minutes down the road, Rock Hall has some more of our favorites!
Ambiance and great food and drink in the heart of historic Chestertown! Check out the courtyard!
20 locals recommend
The Kitchen at the Imperial
208 High StAmbiance and great food and drink in the heart of historic Chestertown! Check out the courtyard!
Casa Carmen Wines
312 Cannon StGreat wines, delicious tapas, in a cozy, personal atmosphere!
Luisa's Cucina Italiana
849 Washington AveA longtime local favorite!
Now called "Deep Blue at Kitty Knight", overlooking Georgetown Marina on the Sassafras River
14 locals recommend
Kitty Knight
14028 Augustine Herman HwyNow called "Deep Blue at Kitty Knight", overlooking Georgetown Marina on the Sassafras River
Winner! (No longer LTO: now, The Retriever) Excellent food and drink! This is one of our personal favorites! Neyah has curated an outstanding collection of spirits, beer, and wine! Great selection of oysters, and try the smashburger.
9 locals recommend
LTO
337 1/2 High StWinner! (No longer LTO: now, The Retriever) Excellent food and drink! This is one of our personal favorites! Neyah has curated an outstanding collection of spirits, beer, and wine! Great selection of oysters, and try the smashburger.
Al makes his own beer and spirits. Great brick-oven pizza!
13 locals recommend
BAD Alfred's Distilling
323 High StAl makes his own beer and spirits. Great brick-oven pizza!
Cafe Sado
205 Tackle CirDelicious Sushi!
Previously located at the Chestertown marina, Fishwhistle is now a 20-minute drive at the nearby Georgetown (NOT DC) yacht basin. Seafood, drinks, etc.
23 locals recommend
Fish Whistle
100 George StreetPreviously located at the Chestertown marina, Fishwhistle is now a 20-minute drive at the nearby Georgetown (NOT DC) yacht basin. Seafood, drinks, etc.
Now called: "Watershed Alley" Upscale fine dining in a beautifully designed and decorated setting! This is a newer restaurant in town and we're all excited about it! One of the owners is a pastry chef, so you know what that means...
13 locals recommend
Watershed Chestertown
337 High StreetNow called: "Watershed Alley" Upscale fine dining in a beautifully designed and decorated setting! This is a newer restaurant in town and we're all excited about it! One of the owners is a pastry chef, so you know what that means...
Blue Bird Tavern
512 Washington AveDo you like a neighborhood feel? This is the place! Great burger selections!
Phat Daddy's
Great authentic ribs, BBQ, and fixin's!
Ford's Seafood
Best place to eat crabs!
Great waterfront location on the bay in Rock Hall! Crabs, etc.
33 locals recommend
Waterman's Crab House
21055 W Sharp StGreat waterfront location on the bay in Rock Hall! Crabs, etc.
Great food, and atmosphere, Tiki-bar and deck seating (inside seating too), friendly service... a very popular place, but they don't take reservations.
Try the Crab Centerpiece appetizer!!!
Blue Heron Oyster House and Inn
Great food, and atmosphere, Tiki-bar and deck seating (inside seating too), friendly service... a very popular place, but they don't take reservations.
Try the Crab Centerpiece appetizer!!!
The old Bay Wolf - brand new in 2024 in Rock Hall, operated by Chris, formerly at 98 Cannon. Check it out!
Flying Decoy Bar and Grill
The old Bay Wolf - brand new in 2024 in Rock Hall, operated by Chris, formerly at 98 Cannon. Check it out!
Tucked away at Haven Harbor South marina, this place is worth searching for! The ambiance and food are among the best around!
Ark & Dove Restaurant
Tucked away at Haven Harbor South marina, this place is worth searching for! The ambiance and food are among the best around!
Food scene
The original Stam's Drugstore, COMPLETELY and artfully remade into this throwback "soda fountain" with delicious homemade ice cream in imaginative flavors and combinations!
8 locals recommend
Stam's Luncheonette
215 High StreetThe original Stam's Drugstore, COMPLETELY and artfully remade into this throwback "soda fountain" with delicious homemade ice cream in imaginative flavors and combinations!
Evergrain Bread Company
201 High StThe best bakery!
Phat Daddy’s BBQ Shack
205 Spring AvenueGreat ribs, barbeque, and fixin's!
Sour Power!! Discover fermentation in ways you never imagined! Dr. Bill and his family will inspire you! Bread, pizza, waffles, pretzels, snacks, classes, and more. Check out their websites. We can't share links here, but look for eatlikeahuman or modernstoneagekitchen (both are .com)
Modern Stone Age Kitchen | Home of Rise By Brianna
236 Cannon StreetSour Power!! Discover fermentation in ways you never imagined! Dr. Bill and his family will inspire you! Bread, pizza, waffles, pretzels, snacks, classes, and more. Check out their websites. We can't share links here, but look for eatlikeahuman or modernstoneagekitchen (both are .com)
Eat in or take-out - this is a popular local restaurant for delicious subs, pasta, and pizza!
15 locals recommend
Procolino's Pizza
711 Washington AveEat in or take-out - this is a popular local restaurant for delicious subs, pasta, and pizza!
Shopping
Newly (and BEAUTIFULLY) renovated and expanded, "Twigs" is now a local destination, with a nicely-curated inventory of gifts, clothes, cards, novelties, art, and much more! See it for yourself!
12 locals recommend
Twigs & Teacups
111 S Cross StNewly (and BEAUTIFULLY) renovated and expanded, "Twigs" is now a local destination, with a nicely-curated inventory of gifts, clothes, cards, novelties, art, and much more! See it for yourself!
Hip women's clothing shop, with accessories, shoes, gifts, and more! One of Gale's favorites!
Bohemia Trading Company
7400 Church Hill RdHip women's clothing shop, with accessories, shoes, gifts, and more! One of Gale's favorites!
Well-put-together collection of "shabby-chic" women's clothes, gifts, re-purposed furniture and more!
Walnut & Wool
321 High StWell-put-together collection of "shabby-chic" women's clothes, gifts, re-purposed furniture and more!
Book Plate
112 S Cross StLike books? This is the place for you!
Open Saturday mornings year-round, this popular outdoor market features the best of local food, arts, and crafts.
14 locals recommend
Marylands Chestertown Farmers & Artisans Market
118 North Cross StreetOpen Saturday mornings year-round, this popular outdoor market features the best of local food, arts, and crafts.
You'll find plenty here to satisfy the discerning chocoholic, whether it be you or someone you want to please! They have a wide selection of delicious gourmet and artisan chocolates and gifts.
Bespoke Chocolate
You'll find plenty here to satisfy the discerning chocoholic, whether it be you or someone you want to please! They have a wide selection of delicious gourmet and artisan chocolates and gifts.