RAR Brewing

Music, drinks, good times - locals have been gathering at this 80-year old former pool hall since summer 2013 to pay homage to the building's history and taste top-notch locally brewed beer. It may now serve up burgers & brewskis instead of strikes & spares, but you still can't beat a place where friendly faces from around town meet for some fun!

Vintage 414

A warm, welcoming atmosphere that offers diverse wines & beers at various price points. Vintage 414 is known for innovative menus and carefully curated wine selections - it truly has something for everyone. Whether you're looking for date night or simply wanting to try something special, Vintage 414 won't disappoint.

Black Water Bakery

At Black Water Bakery, you can select from freshly-prepared breakfast and lunch fare plus a variety of irresistible pastries. From buttery scones to muffins and cupcakes - this place has all your guilty pleasures! And what better way is there to enjoy these delights than with an excellent cup of joe from Chesapeake Bay Roasting Company?

Blue Ruin

An inviting restaurant and watering hole with a friendly vibe. The food is great, but its true forte lies in the incredible cocktails concocted by masterful mixologists - they’ll help you choose from their impressive selection of drinks to find something that's just right for you.

Ava’s Pizzeria

Step into a restored historic building in downtown Cambridge and you'll be transported to an Italian eatery with delicious pizza, Ma’s famous meatballs and an excellent beer selection to top it all off. Come rain or shine - take advantage of the outdoor seating for prime people watching on sun-drenched days!

Bay Country Bakery

Bay Country Bakery has been a hometown favorite for over 30 years—it's where the Eastern Shore of Maryland goes for high quality sweets, from delectable donuts to decadent cakes. And of course their fresh brewed coffee and hot tea selection are sufficient reasons to visit. So stop in and see why this spot is still going strong after all these years!

Choptank River Lighthouse

Sailors have relied on the lighthouse along the Choptank River to guide them safely since it first graced Dorchester County's stunning coastline. Now visitors can enter this exact replica of the original lighthouse to explore a beacon of maritime history and a museum dedicated to honoring local seafaring traditions.

Harriet Tubman Underground Railroad National Historical Park

Delve deep into Harriet Tubman’s roots where an underground resistance movement was born. Tour comprehensive exhibits that are informative yet deeply emotive for visitors looking to learn about this incredible woman’s story. Pro tip - if you plan on taking walks through their beautiful legacy garden or exploring other related sites, arm yourself with bug spray and sunscreen as it can get rather warm & muggy during certain seasons!

Blackwater National Wildlife Refuge

Come experience the wild beauty of over 20,000 acres open to public recreation throughout the year! Hikers and paddlers alike can explore up to 22 miles of breathtaking terrain while wildlife photography enthusiasts can enjoy the 3.6 mile scenic drive winding through 15,000 stunning acres reserved for deer hunting from September-January. Come visit this untouched paradise waiting for you to explore.

Cabin Fever Play Center

The perfect rainy day activity for kids, including a 1,500 sq ft playground structure filled with climbing, obstacle courses, slides, swings, and much more. And be sure to check out their arcade games and ball blaster arena - even the parents won’t want to leave!

Food Lion

A reliable supermarket carrying all the staples you’ll need for your vacation.

Cambridge Wine & Spirits

Your one-stop-shop for all your beer, wine, and spirits needs.

Richardson Maritime Museum

An educational tribute to the rich maritime history of Maryland's Eastern Shore, featuring an impressive collection of boats, artifacts, and exhibits that showcase the region's seafaring heritage.

Sailwinds Park

A destination for boating enthusiasts, with a variety of facilities and amenities for launching, docking, and maintaining boats, as well as scenic trails for hiking and biking.

Dorchester County Visitor Center

A welcoming and informative hub for visitors to the Eastern Shore, featuring a wealth of resources, exhibits, and knowledgeable staff.

KOOL Ice & Seafood Co.

Looking for fresh crabs and seafood? Kools is an authentic, eastern shore wholesaler for your next family crab feast! Make sure you know your sizes and order quick, their fast-paced service style is part of the fun. Don’t forget to grab some mallets and newspaper. 

Choptank Bowling & Billiards

Come to enjoy a variety of games and activities for all ages along with food and drinks to keep the party going.

Suicide Bridge Restaurant

An historic dining experience featuring fresh and locally-sourced seafood and waterfront views, as well as a fascinating backstory that adds to its allure.

Spocott Windmill Foundation

An historic destination that features a beautifully restored windmill that serves as a tribute to the region's agricultural heritage, as well as a variety of exhibits and educational programs that celebrate the important role that farming has played in the region's history and culture.