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Restaurants in Chestertown

Luisa's Cucina Italiana 849 Washington Ave, Chestertown
Luisa's Cucina Italiana
Italian • $$

Luisa's Cucina Italiana

849 Washington Ave, Chestertown, MD 21620

I know this is an Italian restaurant primarily, but they also happen to have the best burgers I’ve had in a very long time. Served on ciabatta bread,...

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  • Superb253 Reviews4.6
The Retriever Bar & The Decoy Bottle Shop 337 1/2 High St #339, Chestertown
The Retriever Bar & The Decoy Bottle Shop
Seafood

The Retriever Bar & The Decoy Bottle Shop

337 1/2 High St #339, Chestertown, MD 21620

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...

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  • Superb90 Reviews4.7
Casa Carmen Wines 312 Cannon St, Chestertown
Casa Carmen Wines
Tapas/Small Plates

Casa Carmen Wines

312 Cannon St, Chestertown, MD 21620

It’s a wonderful local winery. Despite there not being a kitchen the food options are plentiful and delicious. The staff is very friendly and...

  • Delivery
  • Superb123 Reviews4.6
Uncle Charlie's Bistro 834 High St, Chestertown
Uncle Charlie's Bistro
Bistros • $$

Uncle Charlie's Bistro

834 High St, Chestertown, MD 21620

Got lucky veggie of the day was my favorite: Broccolinici.Also was build your burger night which I also love so I made an awesome bacon cheese burger with a...

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  • Superb181 Reviews4.5
Phat Daddy’s BBQ Shack 205 Spring Ave, Chestertown
Phat Daddy’s BBQ Shack
Barbecue

Phat Daddy’s BBQ Shack

205 Spring Ave, Chestertown, MD 21620

As I walked in I was greeted by a very nice young lady. She was very friendly and seemed geniunely happy to be there. I ordered the ribs, mac and cheese, baked...

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  • Superb55 Reviews4.7
Happy Chicken - Bakery, Catering, Cafe 215 Scheeler Rd, Chestertown
Happy Chicken - Bakery, Catering, Cafe
Cupcakes

Happy Chicken - Bakery, Catering, Cafe

215 Scheeler Rd, Chestertown, MD 21620

Just had a great sandwich! I went to order a cake for a party and the smell was just too tempting--ordered grilled ham and cheese on pretzel bread. Oh yum!...

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  • Superb43 Reviews4.8
Watershed Alley 337 High St, Chestertown
Watershed Alley
Seafood

Watershed Alley

337 High St, Chestertown, MD 21620

Very pleasant discovery in Chestertown. We went for lunch but I'll be returning back shortly for dinner. Pork Belly and Tuna Poke were great starters and...

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  • Superb74 Reviews4.6
Procolino's Pizza (Proc’s) 711 Washington Ave #9, Chestertown
Procolino's Pizza (Proc’s)
Pizza • $

Procolino's Pizza (Proc’s)

711 Washington Ave #9, Chestertown, MD 21620

We were in the area shopping and were looking for a quick place for lunch. My husband noticed this pizza shop so we decided to give it a try. We aren't...

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  • Superb179 Reviews4.4
BAD Alfred's Distilling 323 High St, Chestertown
BAD Alfred's Distilling
Pizza

BAD Alfred's Distilling

323 High St, Chestertown, MD 21620

Ended my birthday weekend with awesome pizzas & delicious drinks. Friendly & energetic service. The smoked wings & stuffed poblano peppers were...

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  • Superb68 Reviews4.5
Figg's Ordinary 207 S Cross St #102, Chestertown
Figg's Ordinary
Gluten-Free • $

Figg's Ordinary

207 S Cross St #102, Chestertown, MD 21620

I’m gluten free and I live in chestertown and it took me way too long to discover figgs but I’m so glad I did. I can’t say enough about how nice it is to...

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  • Superb89 Reviews4.4
C-Town Liquors & Deli 601 Washington Ave, Chestertown
C-Town Liquors & Deli
Deli

C-Town Liquors & Deli

601 Washington Ave, Chestertown, MD 21620

My husband just picked up our subs..we moved here 2yrs ago and decided to give this place a try..omg the best..he said everyone was very nice..I can't...

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  • Superb69 Reviews4.4
Jellyfish Joel's Beach Bar 22170 Great Oak Landing Rd, Chestertown
Jellyfish Joel's Beach Bar
Tiki Bar • $$

Jellyfish Joel's Beach Bar

22170 Great Oak Landing Rd, Chestertown, MD 21620

Always fun at JJ, but expect a crowd. Basically it is a bunch of boaters listening to music and having some drinks. If you are from the western shore and want...

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  • Superb63 Reviews4.3
The FREEZE 717 Washington Ave, Chestertown
The FREEZE
Fast Food • $

The FREEZE

717 Washington Ave, Chestertown, MD 21620

Old fashioned soft serve drive-up! (Not to carside delivery--you go in then back out to car.) Lots of opportunity to make your own treat--cherry coke float? no...

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  • Good109 Reviews4.2
China House 711 Washington Ave #31, Chestertown
China House
Chinese • $$

China House

711 Washington Ave #31, Chestertown, MD 21620

I love china house in Chesterton. Best take out food in town. Love the wontons and egg rolls, beef n broccoli, and the poo poo platter that has a little bet of...

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  • Good97 Reviews4.2
Billy's Crabs 1605 McGinnes Rd, Chestertown
Billy's Crabs
Seafood

Billy's Crabs

1605 McGinnes Rd, Chestertown, MD 21620

Two of us shared a dozen crabs. There was a mix of sizes, because "that's the way (they) do it". There were 2 mediums, 2 jumbo, and the rest...

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  • Good51 Reviews4.2
Papa Smurfs BBQ Food Truck 848 High St, Chestertown
Papa Smurfs BBQ Food Truck
Barbecue

Papa Smurfs BBQ Food Truck

848 High St, Chestertown, MD 21620

Got my first taste of Papa Smurf BBQ and it’s safe to say I’ll be back. I got a cheeseburger with everything and it was so fresh and good! Fries were hot...

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  • Superb18 Reviews4.3
Beverly's Family Restaurant 11 Washington Ave, Chestertown
Beverly's Family Restaurant
Family • $

Beverly's Family Restaurant

11 Washington Ave, Chestertown, MD 21620

We stumbled in after a horse show in the area looking for some breakfast. What a great breakfast we got! Would never have expected such a great meal just...

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  • Good126 Reviews4.1
The Kitchen at the Imperial 208 High St, Chestertown
The Kitchen at the Imperial
American • $$

The Kitchen at the Imperial

208 High St, Chestertown, MD 21620

Ate outside in patio as pictured. Menu had a wide variety, prices a little high. It was a busy day in town, staff a little disorganized and made us move...

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  • Good207 Reviews4.1
Cafe Sado 870 High St, Chestertown
Cafe Sado
Sushi • $$

Cafe Sado

870 High St, Chestertown, MD 21620

Was working out of town for a week in Chestertown and stumbled upon Cafe Sado. Ate there every day of the week getting a different meal each day with amazing...

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  • Good167 Reviews3.9
Milano's Pizzeria 6346 Church Hill Rd, Chestertown
Milano's Pizzeria
Pizza • $$

Milano's Pizzeria

6346 Church Hill Rd, Chestertown, MD 21620

We are in Chestertown for a few days, we just wanted a quick dinner and Milano's was the closest. We had a medium margarita pizza, also a nice hot well...

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  • Good137 Reviews3.8
Domino's Pizza 518 Washington Ave, Chestertown
Domino's Pizza
Pizza • $

Domino's Pizza

518 Washington Ave, Chestertown, MD 21620

They close at 11 pm which saved us! We stayed 2 days to visit Chestertown area and we didn’t know most restaurants close at 8 pm! After browsing a lot we...

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  • Good85 Reviews3.6
Arby's 707 Washington Ave, Chestertown
Arby's
Fast Food • $

Arby's

707 Washington Ave, Chestertown, MD 21620

Chestertown Arby's had a really awesome Drive through lady today at 430pm. She took the order very politely and informed us of some issues with our order...

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  • Good89 Reviews3.6
McDonald's 875 Washington Ave, Chestertown
McDonald's
Fast Food • $

McDonald's

875 Washington Ave, Chestertown, MD 21620

believe it's customary to allow the buyer to choose the meal they want to eat. Not argue with a customer. Especially if you're in a manager position....

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  • Good105 Reviews3.5
Taco Bell 709 Washington Ave #2, Chestertown
Taco Bell
Fast Food • $

Taco Bell

709 Washington Ave #2, Chestertown, MD 21620

Personally I know some of the Employees, and I think that although the service can he sloth at times that this restaurant is what you pay for and a delight! I...

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  • Drive-Through
  • Poor67 Reviews2.1