Dorchester News | May 2025
WHAT’S INSIDE: Dive Into Warm-Weather Fun | New Shop! Ice Cream! Plus Attractions Re-Open for the Season | Nation’s Oldest Powerboat Races May 17-18 | May Events | Arts & Music
Dive into warm-weather fun!
There’s nothing like the feeling of being on the water — the gentle breeze on your face, the rhythmic motion of the waves, and the endless horizon stretching before you. In Dorchester County, water is everywhere, offering a sense of peace and a touch of adventure. With 1,700 miles of shoreline and winding waterways, this is a place where you can chart your own course — by kayak, sailboat, or even from a cozy spot on shore. Dorchester County is the perfect place to reconnect with the water — and yourself.
Plan your fun with our 2025 On the Water Guide.
New shop buzz! Ice cream on wheels!
Fresh finds!
The Hive: Art & Goods has its grand opening on May 10! Artful, soulful, and full of charm, this light-filled gallery features handmade goods, fair trade finds, estate sale curiosities, and local art in every medium. Grand opening reception is May 10, 5-8pm, with some of the featured artists, live music, and refreshments. 450 Race St., Cambridge. 443-477-7501. Follow the Hive on Facebook.
Simmons Center Market has a new ice cream truck serving up hand-dipped ice cream and more. Check their Facebook to see the latest schedule.
Lil Bitta Bull BBQ has a grand opening May 2 , 11am-5pm, for their food truck in Hurlock at 101 Delaware Ave.
Seasonal favorites return
Spring is in full bloom, and we're happy to see our Dorchester County seasonal attractions, merchants, and restaurants back in action!
- On-the-water fun – Step aboard Skipjack Nathan of Dorchester, Choptank Riverboats, fishing charters, Capt. Phil Gootee Cruises, or Buyboat Dudley Charters. Paddle and more with Blackwater Adventures. For details, see our On the Water Guide!
- The Choptank River Lighthouse reopens May 1 with free self-guided tours. Open daily, 9:30am-5:30pm.
- Horn Point Lab Tours begin Memorial Day week and run through Labor Day at 10am each Tuesday. Free!
- Cambridge Ghost Walks are back in action on Maryland's most haunted street. This month, they’re set for May 10 and 24.
- Ocean Odyssey Crab House & Seafood Restaurant has re-opened. Open Thursday through Monday; live jazzy music on most Mondays, 6-8pm.
- Blue Point Provision Co. at the Hyatt Chesapeake re-opens Memorial Day weekend.
- Lindy’s Seafood has re-opened. Specializing in Maryland hard crabs and fresh-picked crabmeat. For now, the seafood market is open Friday and Saturday 9am-6pm; Sunday 9am-5pm; soon to expand to seven days a week.
Nation's oldest powerboat races May 17-18
The Cambridge Classic Powerboat Regatta marks its 114th year on the Choptank River in Cambridge on May 17-18, making it the oldest active powerboat race in the United States. Today's hydroplanes and jersey skiffs average between 70 and 170mph! Presented by the Cambridge Power Boat Association, the Hydroplane Racing League, and the Dorchester Chamber of Commerce, this year's race is expected to see about 70 boats. The races happen Saturday and Sunday on Hambrooks Bay off the Choptank River. Watch on land at Gerry Boyle Park at Great Marsh, or from your own boat on the water. (The fleet will raft at Rooster Point. A no-wake zone will be established from Howell Point to the Choptank River Bridge.) Admission is free with a $5 fee for parking. Food and drink, fun for kids. The weekend kicks off with a pre-race concert featuring the classic rock of Tranzfusion on Friday, May 16 at 6pm at Great Marsh Park ($10 parking fee for the concert). Find out more.
Photo below by Tim Mangus.
Swim, bike, run Dorchester: Race season returns
Stretch your limbs and ramp up your motivation by signing up for one of the races or endurance events that happen in Dorchester County! Runners, cyclists, swimmers flock here for events from April to October (and beyond that for training). Whether you’re a weekend warrior or a committed athlete, you’ll find a range of competitive races and friendly, supportive events. This year’s race events include:
- Six Pillars Century Bike Ride - May 10
- Cambridge Crab Run - May 11
- Maryland Freedom Swim - May 31
- IRONMAN 70.3 Eagleman Triathlon - June 8
- Firecracker Kids Triathlon - July 4
- IRONMAN Maryland Triathlon - Sept. 20
- Wild Goose Chase Women’s Bicycle Ride - Sept. 13-14
- GFNY Maryland Cycling Event - Oct. 5
Volunteers needed!
If you're not interested in competing, be a part of the excitement by volunteering! All of Dorchester's race events rely on volunteers, especially the IRONMAN events, which require hundreds of pairs of hands to pull off. To sign up for the next IRONMAN event in June, go to the Eagleman volunteer page, where you can see the range of volunteer positions.
MAY EVENT HIGHLIGHTS
May 1
Emily's Produce opens its strawberry fields for berry picking! The fields open at 9am and close one hour before market closing (5pm weekdays & 4pm weekends).
May 1-3
Find a treasure – antiques, collectibles, tools, furniture, glassware, chinaware, decorations, books, movies, and more. May 1, 4-6pm (for DCHS members only); May 2, 7am-4pm; May 3, 7am-4pm. Proceeds support DCHS.
May 2, 6-9pm; May 3, 4-10pm
This two-night event honors the network of entertainment venues, including here on Pine Street in Cambridge, that provided a space for Black musicians to perform, particularly during the Jim Crow era from the 1930s to the 1960s. On Friday, there's a presentation on the history of the Chitlin’ Circuit, live band, and food including a taste of chitterlings. Saturday is a gala with dinner, live musical tributes to Sarah Vaughn, Billie Holiday, Cab Calloway, Chuck Berry and more. Tickets include admission to both night’s events.
May 3, 6-9pm
Celebrate the new season at Layton’s Chance Winery by burning last year's growth with a huge bonfire, s’mores, wine, live music with Tranzfusion and a food truck. 21+ only.
May 3, 12-5pm
Street festival in downtown Cambridge with live music, drinks, local artists (some with Star Wars-themed designs), craft vendors, fire pits, kids' area. Created by RAR Brewing and organized by Lori Dever of 3ten Art Gallery. On the 500 block of Poplar Street and in the Blue Ruin Gay Street parking area.
May 4, 8am
Last tour until fall! Join a guided birding tour at Blackwater National Wildlife Refuge. Meet at Blackwater Visitor Center parking lot at 8am. Free.
May 6 and 7, 5-7pm
Harvest Drive Greenhouses in East New Market stays open late to donate a portion of proceeds of items purchased between 5 and 7pm to MidShore Meals til Monday on May 6; Warwick Elementary School on May 7.
MAY EVENT HIGHLIGHTS, cont'd
May 7, 7pm
Chief Donna Wolf Mother Abbott of the Nause-Waiwash Tribe of Indians discusses the history of the tribe as well as the tribe’s accomplishments, goals, and annual festival and fundraising activities. At the Dorchester County Historical Society. Part of the South Dorchester Folk Museum lecture series.
May 10, 12-2pm
Layton's Chance Winery hosts this fun class. Ticket price includes heart-shaped charcuterie board, selection of meats, cheeses, jams, pairings, plus complimentary glass of wine/slushie to sip while you create.
May 10, 9am-12pm
Begins at Long Wharf in Cambridge. Register on site at 9am; walk begins 10am.
May 10
This is the first in a series of Cambridge Main Street's Second Saturdays featuring live music, enhanced outdoor dining, sidewalk shopping, and fun for kids! Some Downtown Cambridge streets will be closed to traffic 3-10pm.
May 10, 10am-3pm
Horn Point Lab hosts a fun--filled and educational day designed for middle-school-aged children to explore the wonders of marine science through hands-on activities and interactive demonstrations. Free, but register in advance.
May 11, 12-5pm
Music by Marianne Styles. Moms receive 1 free glass of wine with lunch.
MAY EVENT HIGHLIGHTS, cont'd
May 16-18
This majestic tall ship is set to arrive around 3pm on May 16 at Long Wharf in Cambridge. Offering day sails, evening sails, and free deck tours May 17-18. Approximate departure is 9am May 19. Be sure to buy tickets for the sails in advance!
May 17, 12-4pm
Live music, singing and praying band, vendors, and more. Malone's Church in Madison is Stop #9 along the Harriet Tubman Byway. Before Malone's Church was founded in 1864, the community provided an important social world for Harriet Tubman and her family.
May 22, 5:30-6:30pm
Join the Cambridge Rotary Club to celebrate their American flag display, which honors heroes from military personnel to first responders to healthcare workers. Flags will be on display through Memorial Day at Long Wharf in Cambridge.
May 22, 6-7:30pm (Virtual)
Help envision the future of the Richardson Maritime Museum! They will be holding a facilitated conversation about what the RMM can and should be moving forward, and how to get there. The public is welcome to join in for this virtual meeting via Zoom. RSVP at office@richardsonmuseum.org.
May 24, 9am
$20 per car. Register online or at 9am the day of. Trophies awarded at 3pm. Live music by Golden Touch 1-4pm. At Johnny's Tavern, East New Market.
May 24, 10am-12pm
Join Elusive Tours for a chance to tour three of Dorchester artist Michael Rosato's iconic murals, hear stories and inspiration from the artist, and get behind-the-scenes access to Michael's private studio. Plus an artist-signed print of one of the murals.
MAY EVENT HIGHLIGHTS, cont'd
May 24, 6pm
Bounce house and family fun, food trucks, live music by Loud Moon and Randy Lee Ashcroft & the Saltwater Cowboys, and birthday cake.
May 26, 2pm (Memorial Day)
This Community Players of Salisbury show highlights the men and women who served at home and overseas during the war effort with dramatic readings, narrations, slides, and a band playing WWII music. Free admission; donations welcome. Seating is limited. For reservations, call 443-235-3272.
Memorial Day Ceremonies
May 26, 11am: American Legion Post 91 leads a ceremony at Long Wharf, Cambridge. In case of rain, event will happen at American Legion, 98 Sunburst Hwy., Cambridge.
May 25, 1:30pm: Eastern Shore Veterans Cemetery usually hosts a service at the cemetery, 6827 E New Market Ellwood Road, Hurlock.
May 31, 10:30am-2pm
Dorchester Tourism welcomes summer with live music by Jayla Elise and other local talent, karaoke for kids and adults, the Book Mobile, and displays by various local attractions and organizations. At the Dorchester Visitor Center in Cambridge. Free! Vendors are welcome to set up at the event. To reserve a spot, call the Visitor Center at 410-228-1000. Space is limited.
The Arts in May
Main Street Gallery features guest artist Carla Huber’s oil paintings and monoprints in the show, "2 Ways About It.” Carla is a well known and award-winning plein air painter who lives and maintains a studio in Woolford. Show runs May 2–June 29. All are welome to the artist reception May 10, 5-8pm, with brief artist talk at 6pm.
SAVE THE DATE
3ten Art Gallery has grand opening in their new location with artist reception June 14, Sat 6-9p. Plus a new show: "The Subliminal State" by Lori Dever, and "Variations in Abstraction & Expression" by Sherry Christopher.
Dorchester Center for the Arts has Young People’s Show featuring art from Dorchester County schoolchildren. All are welcome to the Second Saturday Reception May 10, 5 pm, featuring awards presentation. Lady Slipper art shown here by Whitney Waller.
DCA also has a range of classes and workshops, from painting to collage, photography to fun and funky furniture painting to decoy carving, pottery, stained glass. They even have a ukulele group and a fiber group that meet regularly! See the schedule.
Music & Dance in May
For the latest on live music, see the Weekend Roundup on Dorchester Tourism's Facebook and Instagram each Friday.
May 2: Bobby Reed
May 8: Reagan Kent
May 15: Colby Sard
May 16: Chesapeake Sons Duo
May 18: Fuzzbox Piranha
May 22: Sam Pugh
May 29: Bobby Reed
Wednesdays, 5-9pm: Live music with Pete Baker
May 2: Ward Ewing
May 3: Star-Spangled Hustlers
May 9: Karaoke with Chuckie Love
Kids' Karaoke at Johnny's Tavern May 18, 3-5pm.
Fridays, 6:30pm
Local musicians, poets, and comedians are invited to strut your stuff. Every other weekend is a "Praise n Worship" Open Mic. Alcohol-free.
May 6 and 13, 6-9pm
Catch the last of the Open Mic Nights of the season at the Dorchester Center for the Arts! Bring your voice and instrument and join the lineup, or just come enjoy! All are welcome. Admission is free; cash bar and snacks.
Music & Dance, cont'd
May 17
Old Salty’s Restaurant (Hoopers Island) hosts a day of bluegrass with three bands (Billy Harrison & the Haywire, New & Used Bluegrass, Front Porch Orchestra) and local artisans/crafters.
May 17, 4-7pm
Enjoy a free outdoor concert with Jen'z Frenz performing the best of the 60s and 70s. Seating is on the lawn. The event, parking, dockage and adjacent boat ramp are all free. Food, vendors, lawn games for kids. Vienna Waterfront Park, Vienna.
Adult Beginner Tap Dancing with the Eastern Shore Dance Academy on Mondays in May, 6:30-7:15pm.
SAVE THE DATE!
June 21, 5-9pm
This Dorchester Center for the Arts event will feature a buffet, cocktails, a fabulous silent auction, and live music by Jayla Elise. Jayla is a soulful 21-year-old singer-songwriter based in Cambridge, whose music blends the emotive power of R&B and soul. Concert takes place at the Chesapeake Grove Intergenerational Center.
June 21
Get ready to move and groove! Featuring Big Mucci, the Emperor of Line Dance Music. Whether you're a seasoned pro or a beginner looking to learn some new moves, this event will be packed with fun, energy, and community spirit. At Minnette Dick Hall, Cambridge. For tickets, call 443-225-0819.
Dorchester Tourism News
Weekend Update
Find out what's going on around the county – check out our roundup of weekend events that we post on our social media each Friday!
Follow us on social media
Facebook: @I Love Dorchester Heritage & Tourism
Instagram: @Visit Dorchester
Dorchester County Tourism offers a wide selection of free digital brochures on our website, including a Dining Guide, Events Guide, Harriet Tubman Underground Railroad Byway Map & Guide, Cycling Guide, Paddling Guide, Birding Guide, and Heritage Guide. View and download them as PDF files.
Dorchester County Tourism | 2 Rose Hill Place, Cambridge, MD 21613
2 rose hill place, Cambridge, MD 21613