SOUTHERN MARYLAND — It’s starting to feel like summer across Calvert, Charles and St. Mary’s counties, with a packed lineup of events for the first week of May. Enjoy a day that’s free and full of fun at the Solomons Maritime Festival at the Calvert Marine Museum, and celebrate 20 years with waterfront activities, live music, heritage demonstrations and family-friendly experiences that highlight the region’s maritime history and culture.
Celebrate the Kentucky Derby, shop local and enjoy live music, with plenty of ways to get out and explore—including free events like the Safe Streets Teen Summit in Waldorf. Grab your friends and family, plan your week and check out the full list of events below to make the most of it.
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THINGS TO DO IN CALVERT COUNTY
☀️ See our Summer Camp Guide for Southern Maryland here.
🍦 See where Kids Eat Free in Southern Maryland here.
North Beach First Fridays on May 1 (6–9 p.m.), at North Beach Boardwalk – Kick off the season as this monthly bayside celebration returns with local art, live music, shopping and community activities throughout town. Stroll galleries, explore small businesses and enjoy the lively atmosphere that brings North Beach together on the first Friday of each month through October. Free admission.
Flower Moon Howl North Beach on May 1 (8 p.m.), at North Beach Boardwalk, 9023 Bay Ave., North Beach, MD – Kick off May’s Flower Moon during North Beach First Friday with a casual community gathering to watch the moonrise and “howl” together on the pier, offering a fun, laid-back outdoor experience to connect and celebrate the season. Free admission.
3rd Annual Cindy Horsmon Memorial Fun Run for Hospice on May 2 (8 a.m.–1 p.m.), at Horsmon Farm – Community fun run honoring the life of Cindy Greene Horsmon, with proceeds benefiting Hospice of the Chesapeake and the Patient Family Fund. The event supports local patients and families in need, helping cover essential expenses such as rent, groceries and utilities. Ticket required.
Calvert Optimist Club Youth Fishing Derby on May 2 (8 a.m.–12 p.m., rain date May 9), at Scrivener’s Choose & Cut Christmas Tree Farm, 1130 M I Bowen Road, Prince Frederick, MD – Youth fishing event with bait, lunch (hot dogs, chips and drinks) and prizes awarded by age group for largest fish and total weight. Fishing runs 8:30–11:30 a.m., followed by lunch and an awards ceremony. Open to ages 2–18. Free admission; registration required.
Spring Craft Fair & Community Event on May 2 (9 a.m.–2 p.m.), at Huntingtown High School – Annual indoor and outdoor craft fair featuring local vendors, small businesses and food trucks, along with family-friendly activities, raffles and a Mother’s Day basket giveaway. Meet local organizations including the Sheriff’s Office, Fire Department and community groups during this rain-or-shine event. Free admission.
Solomons Maritime Festival on May 2 (10 a.m.–4 p.m.), at Calvert Marine Museum, 14200 Solomons Island Road S, Solomons, MD – A waterfront festival featuring antique boats and marine engines, hands-on demonstrations, seafood preparation exhibits, live music, retriever demonstrations, model boat displays, free cruises and family-friendly activities including toy boat building. Free admission.
Teas & Tiaras: A Mommy & Me Affair on May 2 (10 a.m.), at Fresco Studios, LLC, 10379 Southern Maryland Blvd, Dunkirk, MD – Dress in your royal best for a tea party experience featuring tiaras, crafts, tea service and activities designed for children ages 6 and under and their moms. Enjoy a fun morning of bonding, photos and hands-on creative stations. Ticket required.
LIVE BOXING: Southern MD Smoke 21 on May 2 (3–7:30 p.m.), at Knowledge Boxing Center, 2400 Solomons Island Road South, Prince Frederick, MD– Experience an action-packed afternoon of live boxing featuring a full card of fighters competing in a sanctioned event with multiple viewing options. Ticket required.
A Day at the Derby SoMD Style Fundraiser for People with IDD on May 2 (5 p.m.), at Perigeaux Vineyards & Winery, 8650 Mackall Rd, Saint Leonard, MD – Enjoy an evening of Kentucky Derby-inspired fun featuring dinner, cocktails, bourbon tasting, live Derby viewing, music and raffles, all supporting programs for people with disabilities through The Arc Southern Maryland. Ticket required.
Doggy Tales: Stories of Rescue, Love, and Finding Home on May 3 (3–5 p.m.), at Northeast Community Center, 4075 Gordon Stinnett Avenue, Chesapeake Beach, MD – An inspiring afternoon featuring real rescue stories, a preview of a new PBS documentary, opportunities to connect with adopters and volunteers, plus vendors, giveaways and activities celebrating the impact of animal rescue. Free admission.
Trivia Night on May 6 (6:30 p.m.), at 1936 Bar & Grill, 4165 Mears Ave, Chesapeake Beach, MD – Grab your team and compete in a high-energy trivia night featuring themed rounds, prizes and plenty of food and drinks. Open to teams of all sizes for a fun evening of friendly competition and bragging rights. Free admission.
For more Calvert County events, visit the Calvert County Maryland website.
THINGS TO DO IN CHARLES COUNTY
☀️ See our Summer Camp Guide for Southern Maryland here.
🍦 See where Kids Eat Free in Southern Maryland here.
Law Day on May 1 (9 a.m.–3 p.m.), at Richard R. Clark Senior Center, 1210 Charles Street, La Plata, MD – Adults age 60 and older can meet with an attorney to complete advance directives, including power of attorney, medical orders for life-sustaining treatment and simple wills, while also getting guidance on special enrollment periods and related resources. Free admission.
We Ain’t Tha Onees Comedy Show on May 1 (10 p.m.–1 a.m.), at Tha Ritz, 6971 Indian Head Hwy, Bryans Road, MD – Late-night comedy show featuring a lineup of stand-up comedians, including special guest appearances, with food, drinks and a high-energy atmosphere. Ticket required.
Wee Bean Coffee Roasters 11 Year Anniversary Celebration on May 2 (6 a.m.–7 p.m.), at Wee Bean Coffee Roasters, 6580 Crain Hwy, La Plata, MD – Celebrate 11 years with live music, food trucks, giveaways and specials throughout the day, plus a DJ starts at 4 p.m. Free admission.
17th Annual Market Day at the Historic Port Tobacco Courthouse on May 2 (9 a.m.–2 p.m.), at Port Tobacco Courthouse, 8430 Commerce St, Port Tobacco, MD – Browse local vendors, plants, crafts and handmade goods while enjoying live music from local performers, including Will Yeckley, Rick and Mary Posey and the Charles County Youth Orchestra. Family-friendly event celebrating local history and community. Free admission.
EOD Day 2026 on May 2 (10 a.m.–4 p.m.), at Maryland Veterans Museum at Patriot Park, 11000 Crain Highway, Newburg, MD – Meet current and former explosive ordnance disposal technicians, hear their stories and explore historic and modern equipment used to safely handle explosive threats during this educational and community-focused event honoring their service. Ticket required.
Safe Streets Teen Summit on May 2 (10 a.m.–4 p.m.), at Regency Furniture Stadium, 11765 St. Linus Drive, Waldorf, MD – A free, interactive community event focused on safe driving awareness, featuring driving simulators, giveaways, food trucks, community resources and hands-on activities for teens, parents and families. Free admission.
Glass Blowing Workshop on May 2 (11:30 a.m.–6:30 p.m.), at Apehangers Bar & Grill, 9100 Crain Hwy, Bel Alton, MD – Hands-on glass blowing experience with guided instruction, allowing participants to create items such as ornaments, pendants, flowers, pumpkins and more. Time slots are limited, with small group sessions for each craft. Ticket required.
Opening Day: Bryans Road Farmers Market on May 3 (9 a.m.–1 p.m.), at Western Charles Farmers Market, 6485 Indian Head Hwy, Indian Head, MD – Kick off the season with local vendors, fresh produce, food trucks, crafters and artisans at this community farmers market. A new food truck hub and expanded vendor lineup will be featured throughout the season. Free admission.
Free Spring Bird Walks on May 3 (7:30–10:30 a.m.), at Piscataway MOS Sanctuary, 14300 Hardy Tavern Drive, Accokeek, MD – Join a guided morning walk led by bird experts to learn about local species, with a welcoming, all-ages environment and no experience needed, plus binoculars available upon request. Free admission.
Free Meal up to $15 for Nurses & Teachers at Rucci’s Italian Kitchen on May 6 (11 a.m.–9 p.m.), at Rucci’s Italian Kitchen & Grille, 10579 Theodore Green Blvd, White Plains, MD – Nurses and teachers with valid ID can enjoy a free meal up to $15 with dine-in purchase as a thank-you event. Offer applies to one food item and excludes beverages
For more Charles County events, visit the Charles County Maryland website.
THINGS TO DO IN ST. MARY’S COUNTY
☀️ See our Summer Camp Guide for Southern Maryland here.
🍦 See where Kids Eat Free in Southern Maryland here.
Southern Maryland Spring Festival from April 30–May 3 (various times), at St. Mary’s County Fairgrounds, 42455 Fairgrounds Road, Leonardtown, MD – A longtime community tradition featuring carnival rides, live entertainment, children’s activities, a tractor pull, car show, vendors and local food, offering family-friendly fun while supporting local charities and food banks. Ticket required.
Vintage Vibes First Friday – Leonardtown from May 1–3 (various times), throughout Downtown Leonardtown, MD – Enjoy a full weekend of shopping, live music, art shows, vendor markets and special events as local businesses host First Friday festivities, featuring extended museum hours, drum circles, gallery openings, trolley rides and pop-up experiences across town. Free admission.
Law Day on May 1 (9 a.m.–4 p.m.), at multiple locations in St. Mary’s County, MD – Adults age 60 and older can meet with an attorney to complete advance health care directives, including power of attorney, medical orders for life-sustaining treatment and simple wills, with free assistance available at senior activity centers and the Department of Aging & Human Services. Free admission.
Historic Sotterley Visitor Experience Center Grand Opening on May 2 (10 a.m.), at Historic Sotterley, 44300 Sotterley Ln., Hollywood, MD – Celebrate the opening of the new Visitor Experience Center with expanded exhibits, improved access to the historic site and family-friendly activities, along with the launch of the guided tour season. Free admission.
Drayden African American Schoolhouse Open House on May 2 (11 a.m.–2 p.m.), at Drayden African American Schoolhouse, 18287 Cherryfield Rd, Drayden, MD – Tour one of the nation’s best-preserved one-room African American schoolhouses and learn about its history and role in education in St. Mary’s County. Staff will be on site to answer questions and share information about the restored building. Free admission.
MarylandFest on May 2 (11 a.m.–5 p.m.), at Historic St. Mary’s City, 18751 Hogaboom Ln, St Marys City, MD – A spring celebration of Maryland’s culture featuring food, drinks, live entertainment and family-friendly activities, bringing together history and community in a festive, outdoor setting. Ticket required.
Kentucky Derby Party on May 2 (3–10 p.m.), at Suttler Post Farm Clydesdales, 38750 Chaptico Rd, Mechanicsville, MD – Watch the Kentucky Derby alongside the Clydesdales with an afternoon of live music, food, beverages, games and entertainment, including a performance by Donald Quade and the South Creek Band. Ticket required.
Paint and Sip Unopened Bottle of Wine on May 3 (2–4 p.m.), at Corteau Vineyards, 38713 Golden Beach Road, Mechanicsville, MD – Enjoy a relaxed afternoon painting an unopened bottle of wine while sipping your favorite vino in a laid-back setting. Choose between selections like Bernie’s Blush or Vidal Blanc and create your own custom design to take home. Ticket required.
Law Enforcement Appreciation Day on May 5 (11:30 a.m.), at The White Rose, 21030 Point Lookout Road, Callaway, MD – Join the community alongside the St. Mary’s County Commissioners, Department of Aging & Human Services and Triad/SALT Council as Officers of the Year from multiple agencies are recognized, with honors presented by state and local leaders including the Governor, Maryland Senate and House of Delegates, followed by a complimentary lunch. Free admission.
Free Meal up to $15 for Nurses & Teachers at Rucci’s Italian Kitchen on May 6 (11 a.m.–10 p.m.), at Rucci’s Italian Kitchen & Grille, 22685 Washington St, Leonardtown, MD – Nurses and teachers with valid ID can enjoy a free meal up to $15 with dine-in purchase as a thank-you event. Offer applies to one food item and excludes beverages.
Reflexology with Ruth on May 7 (9 a.m.–4 p.m.), at Garvey Senior Activity Center, 23630 Hayden Farm Ln, Leonardtown, MD – Enjoy a 45-minute reflexology session focused on circulation and balance, with options for head, hands or feet while relaxing in a reclining chair with a jade heating mat. Individual appointments available throughout the day. Ticket required.
For more St. Mary’s County events, check out the Visit St. Mary’s MD website.
SOUTHERN MARYLAND LIVE MUSIC SCHEDULE BROUGHT TO YOU BY LYNN’S MUSIC LISTINGS
Friday – May 1st
4:00pm – Chesapeake Sons – The Wharf – Deale MD
5:00pm – Chris Dean – Greene Turtle Sports Bar – La Plata MD
5:00pm – James Cornett – Mully’s Brewery – Prince Frederick MD
5:30pm – Levi Stephens – Port of Leonardtown Winery – Leonardtown MD
5:30pm – No Go Romeo – Fager’s Island – Ocean City MD
6:00pm – Joseph Norris – Helen’s Cafe _ Leonardtown MD
6:00pm – Wesley Spangler – The TIKI Bar – Solomons MD
6:00pm – Arkansas Williams – Happy Harbor Restaurant – Deale MD
6:00pm – Jason Bishop – Stoney’s Clarkes Landing – Hollywood MD
6:00pm – Chris Turner – Southern Trail Distillery – Mechanicsville MD
6:00pm – Pork Donut – Seabreeze Tiki Bar – Mechanicsville MD
6:00pm – Ryan Forrester Band – Wheel House Beer Garden – North Beach MD
6:00pm – Shaun Gomban – The Local – Hollywood MD
6:00pm – Billy Breslin – Ruddy Duck Brewery & Grill – Solomons MD
6:00pm – Nightcap – Dockside Restaurant & Sports Bar – Deale MD
6:30pm – Will Benthal & Gabe Hurley – Helen’s Cafe – Leonardtown MD
7:00pm – John Luskey – Pirates Cove Dock Bar – Galesville MD
7:00pm – Myles Deep Duo – Brudergarten Beer Garden – Leonardtown MD
8:00pm – 2nd Hand News (Fleetwood Mac) – Running Hare – Pr. Frederick MD
8:00pm – Midnight Sunsets – Toots Bar – Hollywood MD
8:30pm – Mariah Jean – Action Lounge & Billiards – Leonardtown MD
8:30pm – HydraFX – Ollie’s Bar & Grill – La Plata MD
9:00pm – Shane Graham – Betty Russell’s Store & Bar – Valley Lee MD
Saturday – May 2nd
10:30am – Folk Salad – Calvert Marine Museum Maritime Fest – Solomons MD
12:00pm – Boogie Blues Explosion – The Bargain Barn – Hughesville MD
12:30pm – HydraFX – Maryland Fest – Saint Mary’s City MD
2:00pm – No Go Romeo – Vera’s Crab House Lusby MD
2:00pm – Carla Simpson – Port of Leonardtown Winery – Leonardtown MD
2:00pm – Levi Stephens – Robin Hill Farm & Vineyards – Brandywine MD
2:00pm – Lawrence & Miner – Corteau Vineyards – Mechanicsville MD
2:30pm – Shaun Gomban – Xella Winery & Vineyard – Mechanicsville MD
2:30pm – 8 Ohms Band – Maryland Fest – Saint Mary’s City MD
2:30pm – Myles Deep Band – NOVA Live! – Manassas VA
3:00pm – Beer Money – Skipper’s Pier – Deale MD
3:00pm – Wesley Spangler – The Boathouse @ Anchored Inn – Deale MD
5:00pm – John Luskey & Michael Ferro – Happy Harbor – Deale MD
5:30pm – Taboo – Wilderness Run Vineyards – Spotsylvania VA
6:00pm – Byron Ciotter – The Taphouse 1637 – California MD
6:00pm – Paul Van Sickle – Pax River Ale House – Lexington Park MD
6:00pm – Bradley Turner – Southern Trail Distillery – Mechanicsville MD
6:00pm – Monkey Business – Stoney’s Clarkes Landing – Hollywood MD
6:00pm – Southbound 4 – Traders Seafood & Ale – Chesapeake Beach MD
6:00pm – Smoke Signals – Seabreeze Tiki Bar – Mechanicsville MD
6:00pm – Loose Change – Dockside Restaurant & Sports Bar – Deale MD
6:00pm – Midnight Sunsets – Wheel House Beer Garden – North Beach MD
6:00pm – Funkzilla – The TIKI Bar – Solomons MD
7:00pm – Bert & Shawn – Neptune’s Seafood Pub – North Beach MD
7:00pm – Scoglio Duo – Pirates Cove Dock Bar – Galesville MD
7:00pm – WIP Acoustic – The Brass Tap – California MD
8:00pm – Yung Joc – The Rex Theatre – Leonardtown MD
8:00pm – Off The Trax – Toots Bar – Hollywood MD
8:00pm – Sister Midnight – The Tavern – Saint Leonard MD
8:00pm – Swamp Dog Blues Band – Buckets Bar & Grill – Lusby MD
8:00pm – HydraFX – Cryer’s Back Road Inn – Leonardtown MD
8:30pm – Winston – Twisted Bar & Grill – Hollywood MD
9:00pm – Copper Pennies – Apehangers Bar & Grill – Bel Alton MD
Sunday – May 3rd
1:00pm – Joel McGuire – Vera’s Crab House Lusby MD
2:00pm – Byron Ciotter – Robin Hill Farm & Vineyards – Brandywine MD
2:00pm – Gabriel Heisey – Port of Leonardtown Winery – Leonardtown MD
2:00pm – Kody Norris Show – Calvert Elks Lodge – Prince Frederick MD
2:00pm – Just Us – Wharf 38 – Deale MD
2:00pm – SouthBound 4 – Seabreeze Tiki Bar – Mechanicsville MD
2:00pm – Doc Marten Trio – Apehangers Bar & Grill – Bel Alton MD
2:00pm – Girl Crush Acoustic – The TIKI Bar – Solomons MD
3:00pm – Monkey Business – Water View Inn – Bushwood MD
3:00pm – Levi Stephens – Stoney’s Clarkes Landing – Hollywood MD
3:00pm – Kurt Gibbons – Pirates Cove Dock Bar – Galesville MD
3:00pm – Fran Scuderi – Wheel House Beer Garden – North Beach MD
3:00pm – John Luskey – Skipper’s Pier – Deale MD
3:00pm – Ryan Forrester – The Pier River Bar – Solomons MD
3:00pm – 4th Wall Break – Blessing of the Bikes @ Toots – Hollywood MD
3:00pm – Doc Lohn – Dockside Restaurant & Sports Bar – Deale MD
3:00pm – Myles Deep Duo – The Boathouse @ Anchored Inn – Deale MD
4:00pm – Ryan Keith Band – Happy Harbor Restaurant – Deale MD
Monday – May 4th
Tuesday – May 5th
6:00pm – Greg Barrick – Apehangers Bar & Grill – Bel Alton MD
7:00pm – Open Mic w/Derek Norris – Twisted Bar & Grill – Hollywood MD
Wednesday – May 6th
5:00pm – Pete Baker – Ketch 22 Restaurant – North Beach MD
5:00pm – Shaun Gomban – Trifecta Restaurant – Solomons MD
6:00pm – Ryan Forrester – Brick Wood Fired Bistro – Prince Frederick MD
6:30pm – Comedy Open Mic – Twisted Bar & Grill – Hollywood MD
7:00pm – Open Mic w/Steve Nelson – The Tavern – Saint Leonard MD
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