Updated May 2, 2025

Spring has arrived in Dorchester County on Maryland’s Eastern Shore, bringing warmer weather, blooming landscapes, and many opportunities to explore. Whether you’re a nature lover, a history buff, or someone who simply enjoys being outdoors, here are five ways to capture the spirit of spring in Dorchester!

1. Springtime delights: Pick your own berries and more

Head to Emily’s Produce to pick your own juicy strawberries (and blueberries and blackberries as the season goes on) and enjoy farm-fresh delights.  For a deeper dive into local agriculture, take a farm tour (first Sunday of the month) at Pop’s Old Place, a sustainable, century-old farm where you’ll meet heritage livestock and learn about regenerative farming.

SIDE TRIP:
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.

Cycling by Spocott Windmill & Village.

2. Explore the wild side of Dorchester County

Spring is the perfect time to discover the natural beauty of Dorchester County. Whether you're an avid birder or a casual nature lover, Blackwater National Wildlife Refuge offers breathtaking birdwatching opportunities. Beyond birding, Dorchester is also great for cycling. Pedal along quiet, scenic country roads – see our Dorchester Cycling Guide for suggested routes. Bring your own bike or rent a bike through Blackwater Adventures or an e-bike through River Dogs. If golf is more your thing, head to River Marsh Golf Club at the Hyatt Chesapeake Resort – Maryland's leading Eastern Shore golf course, whose finishing holes offer stunning waterfront vistas.

SIDE TRIP:
There's plenty of fishing in Dorchester. Here you’ll find a mix of freshwater, saltwater, and tidal fish species such as rockfish (also known as striped bass), white perch, croaker, black drum, flounder, and many more. Not to mention invasive species such as the northern snakehead and blue catfish. We have expert anglers who are happy to take you out and show you some prime spots. See the latest Fishing Report from the Maryland Department of Natural Resources.

Pride of Baltimore II - Photo by David Sites

3. Get festive with spring events

The warm weather brings forth all kinds of events in Dorchester, from music to history. A few highlights:

Iron Sharpens Iron: Groove City Chitlin' Circuit Tribute: A two-night celebration of the legendary Chitlin Circuit – and its musicians who once performed on Pine Street in Cambridge including Ella Fitzgerald and Cab Calloway – through music, history, and culture. May 2-3

Burning of the Vines: Head to Layton's Chance Winery for a bonfire of last year’s grapevine growth with s’mores, fresh kettle corn, music by Transfusion, and wine. 21 and over. May 3

Tall Ship Visit: The Pride of Baltimore II is coming to Cambridge! While plans are still being finalized, usually they offer sails and deck tours. What an experience to see this reproduction of a typical early 19th-century "Baltimore clipper" topsail schooner! May 16-18

Powerboat Races: The Cambridge Classic Powerboat Regatta is the nation's oldest! Watch speed on the water as the hydroplanes and jersey skiffs average between 70 and 170mph! Best viewing from Gerry Boyle Park at Great Marsh in Cambridge. The weekend kicks off with live music from Tranzfusion on Friday evening, May 16. Races are May 17-18, 10am-5pm

"Take My Hand" mural by local artist Michael Rosato – at the Harriet Tubman Museum & Education Center in Cambridge. Harriet Tubman was born in Dorchester County. Photo courtesy Maryland Tourism.

4. Explore the Mural Trail

Wandering the back roads of Dorchester County is always fun, but it's even more so when you have a goal! So plan to check out part or all of Dorchester's Mural Trail! It's a great way to experience different parts of the county – and to learn about our local history and culture, too. There are more than 20 murals, ranging from the nationally known "Take My Hand" Harriet Tubman Mural in Cambridge to the new Toddville Mural in the far reaches of rural southern Dorchester to the vibrant Women of Dorchester County mural. Check out the Mural Trail.

PRO TIP: 
Get an insider's look at some of the murals by joining Elusive Tours' "Murals & Stories with Michael Rosato" on May 24. Tour three of the Dorchester artist's iconic murals, hear the stories and inspiration from the artist, and get behind-the-scenes access to Michael's private studio.

Crab Cake at Old Salty's Restaurant in Hoopers Island.  Photo by Jill Jasuta

5. Savor Dorchester's freshest flavors

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. You’ll find crab cakes, 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, head 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. For an extra special wine experience, ask about their VIP Tastings and Library Tastings! More of a beer drinker? Founded by Cambridge locals, RAR Brewing creates beers that have become loved nationwide. Stop by their taproom in Downtown Cambridge, where they 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.

PRO TIP:
Pick up local tastes to bring home! The Cambridge Farmers Market is open 3-6pm every Thursday at Long Wharf in Cambridge, offering up local produce, meats, cheeses, and more.

Dorchester truly comes alive in the spring, offering an exciting mix of outdoor adventures, fresh flavors, and lively events. Whether you’re a first-time visitor or a longtime local, there’s no better time to embrace the season. So get outside, explore, and celebrate spring fever in Dorchester!