Published April 29, 2024

An overnight or two-night getaway with a change of scene, beautiful scenery, and friendly folks can make all the difference when it comes to relaxing and recharging. Dorchester County on Maryland’s Eastern Shore offers plenty of all that. Here are a few ideas to make it easy to get away from it all for a weekend (or weekday) trip!

Head to the Islands  |   House & Garden Weekend  |  The Farm Experience  |  Eat Local Tour  |  Weekend on the Water  |  Go Wild for the Weekend

Hoopers Island Sunset | Visit Dorchester

Classic sunset on Hoopers Island

Head to the Islands

Head to the islands without breaking the bank – or even getting on a plane! Dorchester County is home to Taylors Island and Hoopers Island on the west side. These oases of quiet and charm offer an escape from the hurried day to day. Warning: There are no gas stations or charging stations, so be sure to fuel up/charge up before you make the drive! (Without any stops, it’s about 50 minutes from the Dorchester County Visitor Center near Route 50 in Cambridge to the southern end of Hoopers Island.) The drive there is half the fun. As people around here say, “It’s not the end of the world, but you can see it from here!” One of the highlights is the causeway between Upper and Middle Hoopers Island. This narrow spit of land is not much wider than the road itself, which winds for nearly two miles with the Chesapeake Bay on your right and the Honga River on your left. You might even be lucky enough to see brown pelicans hanging out in droves.

There’s also a lot of history to explore. Right over the Slaughter Creek Bridge, make a quick stop at the Becky Phipps Cannon and learn about the 1812 Battle of the Ice Mound. Further along, stop by the collection of historic buildings maintained by the Grace Foundation, including a schoolhouse from 1785, a 1700s chapel, and a 1873 church.

Home to watermen’s villages, this area’s handful of restaurants boast local seafood – and water views. Try Boats & Hose or Old Salty’s Restaurant all year round for crab cakes and more. Palm Beach Willie’s is open seasonally on the water.

For overnight accommodations, consider Riverside Lodge for a down-home, all-inclusive experience, or an airbnb or VRBO based in Taylors Island, Fishing Creek, or Hoopersville.

Maryland House & Garden Pilgrimage 2024 – Dorchester County

The Maryland House & Garden Pilgrimage in Dorchester County includes six historic homes and sites and three new homes

House & Garden Weekend

Make plans for the Maryland House & Garden Pilgrimage, which comes to Dorchester County on June 1 from 10am to 5pm. Stops on the tour include six historic homes and sites and three new homes, all waterfront and all located in the “Neck” district in western Dorchester County. (A 22-square mile area, “the Neck” has 125 miles of shoreline with one road leading into it, and every divergent road ending at the water.) Properties include a 1750 Georgian farmhouse, an 1863 family farmhouse, an 1850s chapel, a historic windmill and re-created 1800s village, a modern waterfront retreat, and more. Enjoy a homemade Eastern Shore lunch at the Neck District Volunteer Fire Company (purchase separately). Buy tickets.

Look for a vacation rental in the Neck District on airbnb or VRBO, or stay at a hotel in Cambridge, a 20-minute drive from the fire hall. If you’d like to remain in the area for dinner after the tour, head to the Neck District Grill, located in a historic former general store (the Lewis Country Store). The limited menu dinner is available only on Friday and Saturday evenings.

While you’re here, explore home and garden decor and art for your home at some of Cambridge’s local indie (independently owned) shops including AT Home, Bay Country Shop, Shorelife Home & Gifts, Butterfly Boutique, Main Street Gallery, 3ten Creative Design & Gift Gallery, Dorchester Center for the Arts, Mowbray’s Garden Center, and Vintage Venue. Or go antiquing at Antique Alley, Bay Country Antiques, Dark Horse Antiques, Heart of Dorchester Antiques.

Strawberry picking at Emily's Produce in Cambridge.

Strawberry picking at Emily’s Produce in Cambridge.

The Farm Experience

Agriculture has been a mainstay in Dorchester County for many generations – back to the days when Native Americans were the earliest farmers and watermen. For some background, head to the Dorchester County Historical Society, Check out the 18th century strong house, beaten biscuit machines, an early McCormick reaper, and other artifacts about farming and canning. Then head out to see how farming has evolved today.

Emily’s Produce is owned by a local family that’s been farming here for seven generations. It re-opens for the season on April 11 with much more than local produce. There are also prepared foods and baked goods; goats, bunnies and chickens; and a play area for the kids. As the season continues, look for U-Pick strawberries, blueberries, blackberries, cut flowers, and in the fall, pumpkins and a corn maze.

Pop’s Old Place,  a small century farm that raises grass-fed and finished beef, lamb, woodland pork, and free-range laying hens. The husband-and-wife owners focus on soil health, animal welfare, and environmental stewardship. They  sell their grass-fed beef, lamb, pork, honey, and eggs to the public from our On Farm Market. On the first Sunday of the month, join their 9am Farm Tour to learn more about their farming practices while following along on their morning chores. (Register at

Vintage Family Farms in Hurlock has finished up its U-Pick tulip season, but later in the season, they’ll offer other kinds of flowers for picking, along with bunny snuggling, vintage games, and more. Keep up with the latest on Facebook or Instagram and reserve here.

Cambridge Municipal Yacht Basin - Photo by Jill Jasuta

Morning light at the Cambridge Municipal Yacht Basin.

Weekend on the Water

Dorchester County’s more than 1,700 miles of shoreline, flat waters, and countless creeks and coves make for great exploring by water – whether or not you have your own vessel. For overnight stays, consider the Hyatt Regency Chesapeake Bay Resort, with 342 acres right on the Choptank River. They also have a marina and offer water sports after Memorial Day.

For kayaking, canoeing and stand-up paddleboarding, there are more than 30 miles of established, charted water trails. You can put in at many spots around the county at one of more than a dozen designated soft launches. We have put together some suggested paddling routes, from 10 to 55 miles, throughout the county in our Dorchester Paddling Guide. It also includes info on kayak/SUP rental.

For boaters, there are more than two dozen free boat ramps around the county. Check out the local marinas, from the Municipal Yacht Basin – within walking distance of the shops and restaurants of Downtown Cambridge – to River Marsh Marina, which includes access to the amenities of the Hyatt Regency Chesapeake Bay. Next to the Municipal Yacht Basin is the Cambridge Yacht Club. And of course, there are plenty of waterways for exploring. Learn more.

If you don’t have your own boat, no worries!

  • Join a cruise (June through October) on the Skipjack Nathan of Dorchester, an authentic wooden sailboat called a skipjack, designed for oyster harvesting.
  • Hop aboard a riverboat for a crab feast cruise, lunch, dinner, or sightseeing cruise with Choptank Riverboats.
    (May through October)
  • Join an on-the-water cruise to see some of the Chesapeake Bay’s lighthouses with Captain Phil Gootee.
  • Charter the historic 1938 Chesapeake buyboat Dudley.
  • Charter a fishing boat with an experienced, knowledgeable captain. See the options.
  • Rent kayaks and SUPs through Blackwater Adventures, either at their Blackwater National Wildlife Refuge location or at the Hyatt Regency Chesapeake Bay, where they also offer rentals of other watercraft, from pedal boats to powerboats.

Plan your trip around a boating event, such as the Cambridge Classic Powerboat Regatta – the nation’s oldest continuously powerboat race – May 18-19, 2024 or Thunder on the Choptank July 20-21, 2024. Another local favorite are boat docking contests, including the Taylors Island Boat Docking Challengel on Aug, 25, the Waterman’s Rodeo on Hoopers Island in early September, and the Extreme Boat Docking Contest late September.

Crab Cake at Old Salty's Restaurant - Dorchester County, MD - Photo by Jill Jasuta

Classic crab cake at Old Salty’s Restaurant on Hoopers Island

Eat Local Tour

Eat your way around Dorchester County! With our many waterways and a long history with the seafood history, Dorchester is known for its fresh blue crab, oysters, and fish from local waters. Not to mention local produce such as sweet corn and tomatoes.

Stay overnight at Cambridge House Bed and Breakfast, an 1847 sea captain’s manor located a stone’s throw from the Choptank River where you can watch watermen bring in their harvest. The bed and breakfast is an easy and scenic stroll down historic High Street to Downtown Cambridge’s restaurants.

Start with breakfast at charming Black Water Bakery, which features a full breakfast menu (locally sourced) – from a crab omelet to a breakfast quinoa bowl to made-in-house pastries. Then there’s a host of eye-opening coffee drinks, and morning-friendly adult beverages such as a build-your-own mimosa or Bloody Mary. On your way out, cross the street and head down the brick alleyway to see the mesmerizing “Take My Hand” Harriet Tubman Mural, which has drawn visitors from around the country.

For lunch or dinner, local, delectable crabmeat is hard to beat. You’ll find crab cakes (pictured above, the crab cake at Old Salty’s), crab balls, crab dip, and crab everything on many Dorchester County restaurant menus. Or go for the authentic Maryland experience of tearing into hardshell crabs. It takes longer, but it’s worth it! For hard-shell crabs, drive to Suicide Bridge Restaurant, Ocean Odyssey Crab House & Seafood Restaurant, or join a Choptank Riverboats crab feast cruise (advance reservations required). Oysters are also on the menu in many restaurants – our locally farmed oysters means they’re available all year long.

And yes, we’ve got locally crafted beverages, too. Spend the afternoon at Layton’s Chance Vineyard & Winery – the Mid-Atlantic’s first craft winery – located on a farm that’s been in the Layton family since 1948. Stroll through the vineyard and farmland, relax on a rocker with one of their 20 wines while the kids let loose in their outdoor play area. Founded by Cambridge locals, RAR Brewing creates beers that have become nationwide. Stop by their taproom in Downtown Cambridge, where they’ve expanded to also offer an eatery (Chessie Burger) with food truck-driven fast food; LabRaRtory, with specialty cocktails in a lounge-like atmosphere; and the Dive Club, a delight for the senses that makes you feel you’ve just stepped aboard Captain Bernard’s old ship.

Birding at Blackwater National Wildlife Refuge in Dorchester County, MD | Visit Dorchester

Birding at Blackwater National Wildlife Refuge.

Go Wild for the Weekend

Dorchester County is known for its great birdwatching, especially at Blackwater National Wildlife Refuge (home to one of the highest populations of eagles on the East Coast). The refuge contains one-third of Maryland’s tidal wetlands and has been called one of the “Last Great Places” by the Nature Conservancy.

You can also use our Dorchester Birding Guide. You can even combine birding with history during a Birding the Harriet Tubman Byway tour, hosted by Delmarva Birding Weekends and Harriet Tubman Tours (Harriet Tubman was born in Dorchester County).

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