1
Main Street Ice Cream Parlor
American restaurant
👍👍 Great place to stop and eat breakfast or to grab ice cream. Store has a lot to offer
$$ $$
4.80 (545 reviews)
2
Luisa's Cucina Italiana
Italian restaurant
👍👍 The best dine-in Italian Restaurant in Chestertown! They have excellent service, the wait staff are amazing! Their food is delicious and has HUGE portions! They accommodated our birthday party of 14 guests! Everything was delicious! We love going there!
$$ $$
4.60 (780 reviews)
3
Procolino's Pizza (Proc’s)
Pizza restaurant
👍👍 By far the best pizza in Chestertown. Authentic Italian food; straight from Italy! We don't eat here as often as we'd like, however that's because it's simply the best around and we like to save it as a treat for when we have a little extra cash or a special occasion.
Side note: if you need quick m...
$$ $$
4.60 (746 reviews)
4
Wilmer Park
Park
👍👍 Wow, a park with all features in working order. I don't know how new this park is but it seems very nice and well kept up with. Good for toddlers to teens.
4.60 (263 reviews)
5
Evergrain Bread Company
Bakery
👍👍 Words can’t express how much I love this place. Small town vibes, high school kids working the counter, delicious pastries and the best iced matcha latte I’ve found in Maryland. Try the lavender iced matcha latte, everknots (addicting), and sun buns! I also liked my breakfast sandwich but wish it ha...
$$ $$
4.60 (242 reviews)
6
The FREEZE
Restaurant
😠 Better service at a McDonald's; at least the staff smiles there. Bought a soda and ice cream cone and the lid wasn't on the cup properly. Soda went everywhere and I helped clean the counter. The solemn looking young girl literally said "You can go." I said I guess I have to buy another soda? She jus...
4.50 (293 reviews)
7
Flagship Premium Cinemas
Movie theater
Neighborhood standby showing new movies with stadium seating, plus rewards for frequent guests.
4.50 (288 reviews)
8
The Bullhouse
Restaurant
Elevated Latin-American comfort food & daily happy hour specials in an elegant, heritage building.
$$ $$
4.50 (239 reviews)
9
Phat Daddy's
Barbecue restaurant
👍👍 First time visiting, will be back! Everyone was super friendly and welcoming. We order the pulled pork sandwich with fries, a cheese quesadilla and mac & cheese. Everything was delicious!
$$ $$
4.60 (143 reviews)
10
Cafe Sado
Sushi restaurant
😠 Been to Cafe Sado before and it was great, loved the atmosphere and food. Finally got a chance to come back and a lot has changed...the table was sticky and the chair was tattered, the lemonade was watery, the sushi didn't taste as fresh, the fried ice cream which is our favorite didn't have the cri...
$$ $$
4.30 (458 reviews)
11
Blue Bird Tavern
Bar
👍 Pretty good place to grab a quick lunch, appetizer or a drink with friends. One of the few sit down places open for Monday lunch. Huge bar that I would have loved to belly up to with a couple of buddies. Seems like a locals spot...no frills but good sandwiches and everyone was super friendly!
$ $$$
4.40 (255 reviews)
12
JJ's Deli & Liquors llc
Liquor store
👍 I really enjoy the deli foods here and the people are very nice and welcoming. And there also isn't a long wait time for your food so it's really convenient.
$$ $$
4.60 (133 reviews)
13
The Retriever Bar & The Decoy Bottle Shop
Bar
👍👍 Tucked into the quaint streets of historic Chestertown, MD - The Retriever is a little gem. Long comfortable bar with a lively atmosphere and a focus on excellence. Top notch oyster selection, curated cocktails, thoughtful (and unique) wine selection offered by the knowledgeable staff. ‘Anothe...
4.80 (90 reviews)
15
Kent County Family YMCA
Fitness center
👍👍 Friendly and helpful staff, great assortment of classes, and the stay and play is great for kids!
4.80 (81 reviews)
18
Garfield Center for the Arts at the Prince Theatre
Performing arts theater
👍👍 Small intimate theater with balcony and comfortable chairs downstairs that could be moved if a person needed more room. Small concession area that sold beer, sodas, bottled water and snacks. I've never seen a stage that had a huge Lazy Susan where the whole set could be turned around in 10 seconds,...
4.80 (74 reviews)
20
Play It Again Sam
Restaurant
👍👍 Nice cozy setting... food was good. They converted the norweigian sandwich to a salad with gluten free bread on the side. Would go again.
$ $$$
4.30 (198 reviews)