SOUTHERN MARYLAND — Ready to get out of the house and find something fun to do? From live music and local history to family activities and community events, there’s no shortage of ways to get out and enjoy Southern Maryland this week.
Highlights include the free Drayden African American Schoolhouse Juneteenth Open House in St. Mary’s County, the Job Search: Find the Right Freelance Jobs workshop hosted by 36 Virtual in Leonardtown, Alan Jackson tribute at Rod ‘N’ Reel Resort and tickets now on sale for Almost Queen with Separate Ways The Band at the Calvert Marine Museum Waterside Pavilion.
Check out our Southern Maryland Summer Concert Guide — concerts have already begun!
Looking for even more? Visit The BayNet Events Calendar for additional happenings and to add your event to be featured across Calvert, Charles and St. Mary’s counties.
THINGS TO DO IN CALVERT COUNTY
☀️ See our Summer Camp Guide for Southern Maryland here.
🍦 See where Kids Eat Free in Southern Maryland here
The Alan Jackson Experience at Rod ‘N’ Reel Resort on June 5 (7 p.m.), The Bandshell at Rod ‘N’ Reel Resort, Chesapeake Beach — The internationally recognized Alan Jackson tribute act takes the stage as part of the Rock the Dock Summer Concert Series at the waterfront resort. Tickets required.
Dried Flower Shadow Box Workshop on June 5 (6–8 p.m.), WhataBoba, 232 Town Square Drive, Lusby — Create a custom shadow box using dried flowers, embellishments and backgrounds; all supplies and instruction included. Tickets required.
Annmarie After Hours on June 5 (5–7 p.m.), Annmarie Sculpture Garden & Arts Center, 13470 Dowell Road, Solomons — Extended evening hours celebrating a new exhibit opening, with live music, gallery tours, sculpture garden access and a food truck on site. Tickets required. Members free.
Bake Sale Benefiting the Humane Society of Calvert County on June 6 (8 a.m.–2 p.m.), Sneades Ace Hardware, 1750 Prosper Lane, Owings — Stop by for fresh-baked goods with proceeds benefiting the Humane Society of Calvert County. Additional dates: Sept. 12 and Nov. 14. Free admission.
Jack & Juni Warehouse Sale on June 6 (10 a.m.–5 p.m.), Jack & Juni, 7620A Investment Court, Owings — A massive warehouse reset sale with 50,000 items at 40% off — clothing, gear and toys in sizes newborn to 14. VIP early access 10 a.m.–noon includes priority stocking and gift card; public entry noon–5 p.m. Free admission noon–5 p.m. VIP tickets required.
National Trails Day & Launch of the Parkers Creek Heritage Trail at ACLT on June 6 (10 a.m.–3 p.m.), American Chestnut Land Trust North Side Trailhead, 676 Double Oak Road, Prince Frederick — Celebrate National Trails Day and the official launch of the Parkers Creek Heritage Trail with guided hikes, educational exhibits, a living history performance, games, crafts and family-friendly activities. Free admission.
Speed Dating at Mully’s Brewery on June 6 (4 p.m.), Mully’s Brewery, 141 Schooner Lane, Suite 15, Prince Frederick — Meet someone new over good conversation and discounted drinks at this structured speed dating event for ages 25–40. Pre-registration required
Children’s Day on the Farm at Jefferson Patterson Park & Museum on June 7 (11 a.m.–4 p.m.), Jefferson Patterson Park & Museum, 10515 Mackall Road, St. Leonard — A full day of live performances, crafts, games, wagon rides, food vendors and exhibits exploring rural life past and present. Free admission.
Outdoor Clay Date at Annmarie Sculpture Garden & Art Center on June 7 (1–3 p.m.), Annmarie Sculpture Garden & Art Center, 13470 Dowell Road, Dowell — Make a wall planter or pocket outdoors in the park using slab, coil and texture techniques; all projects fired in the kiln for pickup. An adult must participate with children. Registration required. Tickets required.
CalvertHealth Farmers Market on June 9 (2–5:30 p.m.), CalvertHealth Medical Center, 130 Hospital Road, Prince Frederick — Shop fresh local produce and goods from Calvert County farms in a vibrant community setting. Free admission.
America 250 Rock Painting Event on June 9 (11:30 a.m.–3:30 p.m.), The Tea Nook at Butterflies and Wishes Tea and Sweets, 3819 Harbor Road, Chesapeake Beach — Drop in weekly to paint patriotic rocks in celebration of America’s 250th anniversary. 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.
Jaycee’s Purse Bingo Fundraiser on June 5 (doors 4:30 p.m., bingo 6:30 p.m.), Waldorf Jaycee Community Center, 3090 Crain Highway, Waldorf — Purse bingo fundraiser benefiting the Humane Society of Charles County with over 20 chances to win, plus pull tabs and raffles. Tickets required.
Family Friday Night at Game Lab Arcade Every Friday (2–8 p.m.), Game Lab Arcade, St. Charles Towne Center Mall, 11110 Mall Circle, 2nd Floor near JCPenney, Waldorf — Unlimited arcade fun, Nerf battles, classic and modern games with Family Friday Night specials available. Tickets required.
Sip & Paint Murder Mystery by Seekme4events Production on June 5 (6–10:30 p.m.), Old Waldorf School, 3074 Crain Highway, Waldorf — A sip-and-paint event with a murder mystery twist; doors open at 6 p.m., brush strokes begin at 7 p.m. Tickets required.
Joe Falero Band Summer Concert at the Town of La Plata on June 5 (7–9 p.m.), Town Hall Lawn, 305 Queen Anne Street, La Plata — Free outdoor concert series featuring a rotating lineup of live music including pop, rock, Latin, jazz, country and more. Bring lawn chairs and enjoy food vendors all season long. Free admission.
Wood and Canvas Family Workshop at AR Workshop La Plata on June 6 (11 a.m.–2 p.m.), AR Workshop La Plata, 317 Charles Street, La Plata — A two-hour family DIY experience creating a unique home decor item using paints, stains and guided instruction. Ages 6 and up; limited seating. Tickets required.
June Walk Charles County Walk with Healthy Charles County on June 6 (11 a.m.–noon), Tilghman Lake Park, 10598 Box Elder Road, La Plata — A one-mile flat dirt and gravel trail walk hosted by Healthy Charles County; all fitness levels welcome. Wheelchair and stroller friendly; leashed dogs welcome. Rain or shine. Free admission.
Read Between the Vines Book Fair at JaneMark Winery and Vineyard on June 6 (noon–4 p.m.), JaneMark Winery & Vineyard, 15200 Baden Naylor Road, Brandywine — Browse local authors and vendors, enjoy live music from John Cain (2–5 p.m.) and grab a bite from Heidi’s Eats food truck among the vines. Free admission.
The Humane Society Presents: Jeepers Creepers on June 6 (2–3 p.m.), P.D. Brown Memorial Branch Library, La Plata — Learn about the importance of creepy crawlers in our ecosystem with the Humane Society of Charles County. Free admission.
Dome Shows at James E. Richmond Science Center on June 6, 10 & 11 (various times), James E. Richmond Science Center, 5305 Piney Church Road, Waldorf — Evening fulldome shows include a short seasonal planetarium presentation. Interactive exhibits and NOAA Science on a Sphere also available; doors open 30 minutes before showtime. Tickets required.
Sensory Social at La Plata Branch Library on June 9 (2–3 p.m.), La Plata Branch Library, La Plata — A monthly sensory-friendly social featuring activities specially cultivated for sensory-seeking youth. Recurring: July 7, Aug. 11 and Sept. 8. Free admission.
Golden Nuggets Bingo at Chick-fil-A Smallwood Drive on June 10 (9:30–10:30 a.m.), Chick-fil-A Smallwood Drive, 3710 Crain Highway, Waldorf — Bingo starts promptly at 9:45 a.m. with prizes and Chick-fil-A favorites. Bingo cards are limited. Free admission.
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.
Happy Hour at Barefoot Farms on June 5 (5–9 p.m.), Barefoot Farms, 21851 Oakley Road, Avenue — Kick off summer with live music from Bryon Ciotti, food from Barkin’ Dogs, drinks from Sippin’ Dirty and u-pick blueberries on the farm. No parking fee. Tickets required.
Raining Cats & Dogs Community Art Show Opening Reception on June 5 (5–8 p.m.), St. Mary’s County Arts Council Gallery & Gift Shop, 22660 Washington Street, Leonardtown — Meet the artists at this First Friday opening reception featuring a paint-and-glaze activity benefiting Feral Cat Rescue of Southern Maryland. Free admission.
First Responder First Friday and Saturday Concert at the Town of Leonardtown on June 5–7, Leonardtown Square and Wharf, Leonardtown — First Friday Weekend features shopping, dining and a “Raining Cats & Dogs” fundraiser benefiting Feral Cat Rescue, plus a free Saturday evening honoring first responders with live music, food and waterfront views. Wharf parking is handicap only; park downtown and take the trolley. Free admission.
Weekend Fun at Corteau Vineyards on June 5–6, Corteau Vineyards, 38713 Golden Beach Road, Mechanicsville — Kick off the weekend with Trivia Night on June 5 (6–8 p.m.), then return Saturday, June 6 (2 p.m.), for live music from Joe Cox among the vines. Free admission.
Ballet Caliente Presents: In Pursuit of Happiness on June 5–6 (6–8 p.m.), Nancy R. & Norton T. Dodge Performing Arts Center, 47855 College Drive, St. Mary’s City — Ballet Caliente performs a new work celebrating the ideals of Life, Liberty, Freedom and Happiness through vignettes depicting American cultural and historical milestones. Tickets required.
First Saturday of the Month Market Series at Town Market LLC on June 6 (9 a.m.–4 p.m.), Town Market LLC, 22675 Washington St., The Bell Building Unit 106, Leonardtown — Shop local crafters, apparel, baked goods, jewelry, tumblers and more at this monthly vendor market in downtown Leonardtown. Free admission.
Youth D&D at Swords and Spoons on June 6 (10 a.m.–1 p.m.), Swords and Spoons, 22599 MacArthur Blvd., Suite 126, California — Youth Dungeons & Dragons drop-in for ages 8 and up; all levels welcome. Just bring your dice. Tickets required.
GMHS SGA’s 4th Annual Nest Fest on June 6 (11 a.m.–3 p.m.), Great Mills High School, 21139 Great Mills Road, Great Mills — A family-friendly community event featuring entertainment, music, games and items from local businesses. Free admission.
Indoor-Outdoor Yard Sale at St. Andrew’s Thrift Shop on June 6, St. Andrew’s Episcopal Church, 44078 St. Andrews Church Road, California — Shop lamps, quilts, lighting, décor and more at the St. Andrew’s Thrift Shop indoor-outdoor yard sale. Doors open 8 a.m.–5 p.m. Thursday and Friday; 8 a.m.–noon Saturday. Free admission.
Drayden African American Schoolhouse Juneteenth Open House on June 6 (11 a.m.–2 p.m.), 18287 Cherryfield Road, Drayden, MD 20630 — Visit one of the nation’s best-preserved one-room African American schoolhouses during a free Juneteenth open house hosted by the Drayden African American Schoolhouse, a St. Mary’s County museum site. Tour the restored schoolhouse across four open dates in honor of Juneteenth. Free admission.
Spring Saturdays at Historic St. Mary’s City on June 6 (noon–3 p.m.), Historic St. Mary’s City, 18751 Hogaboom Lane, St. Mary’s City — Explore Maryland’s first capital through guided tours highlighting archaeology, landscapes and iconic structures. Registration required upon admission purchase. Ages 6 and under free. Tickets required.
Summer Fest at T Farm on June 6 (3–9 p.m.), T Farm, 26850 Coolie Way, Mechanicsville — A community faith gathering featuring multiple live bands playing praise music, speakers, ministries from across the tri-county area, food trucks, games, face painting, silent auctions and crafts. Free admission.
Southern Maryland Boat Club’s Rumble on the River on June 6–7, Piney Point Landing, 17139 Piney Point Road, Piney Point — Watch vintage race boats thunder across Breton Bay during two days of free boat racing hosted by the Southern Maryland Boat Club. Visit the pits during the designated lunch hour to meet drivers and see the boats up close; food truck on site both days. Admission is free.
Flea Market at Pier450 on June 6–7 (9 a.m.–3 p.m.), Pier450, 48342 Wynne Road, Ridge — Browse vintage furniture, lamps, crystal, silver, china, jewelry and more at this weekend flea market featuring curated treasures from designer Paul Haynes. Free admission.
Job Search: Find the Right Freelance Jobs on June 10 (6–7:30 p.m.), The Inn at Leonardtown, 41655 Park Ave., Leonardtown — Learn search strategies, filters and scam detection for Upwork and leave with actual jobs ready to apply to. Registration required. Register at 36virtual.com.
Maryland PFML Webinar: What Trusted Advisors Need to Know Now on June 11 (1–2 p.m.), Virtual — A complimentary educational webinar presented by ShelterPoint Insurance and hosted by Waring-Ahearn Insurance covering Maryland’s new Paid Family and Medical Leave program requirements for employers, CPAs, bookkeepers, financial advisors and HR professionals. Free admission.
An Evening with the Clydesdales at Suttler Post Farm on June 11 (4–8 p.m.), Suttler Post Farm, 38750 Chaptico Road, Mechanicsville — Spend an evening with the Clydesdales featuring a special performance by the Southern Maryland Drill Team Horses, plus food trucks, local vendors and meet-and-greet opportunities. Admission free.
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 29th
4:30pm – Bushwood Mill Band & Jam – Summerseat Farm – Mechanicsville MD
4:30pm – Chris Beard – Port of Leonardtown Winery – Leonardtown MD
5:00pm – Joseph Norris – Morris Point Restaurant – Abell MD
5:00pm – Mike Mead & Eric Wolf – Mully’s Brewery – Prince Frederick MD
5:00pm – Jack Allen – Greene Turtle Sports Bar – California MD
5:00pm – Brian Grumbine – Greene Turtle Sports Bar – La Plata MD
5:00pm – Monkey Business – Running Hare Winery – Prince Frederick MD
5:00pm – Chris Button – Happy Harbor Restaurant – Deale ND
6:00pm – Billy Breslin – Angler’s Seafood Bar & Grill – Solomons MD
6:00pm – Shaun Gomban – The Local – Hollywood MD
6:00pm – Kevin Lee – Trueman Vineyards & Winery – Aquasco MD
6:00pm – Funkzilla Unplugged – Stoney’s Clarkes Landing – Hollywood MD
6:00pm – Myles Deep Duo – Dockside Restaurant & Sports Bar – Deale MD
6:00pm – Tommy McGee Band – Bluefish Pub – Solomons MD
6:00pm – HydraFX – The TIKI Bar – Solomons MD
6:30pm – Southern Echoes – Seabreeze Tiki Bar – Mechanicsville MD
6:30pm – Audra Keeler & Johnny Brown – Ruddy Duck Brewery – Solomons MD
7:00pm – South Creek – Brudergarten Beer Garden @ SOF – Leonardtown MD
7:00pm – Freshly Squeezed – Pirate’s Cove Dock Bar – Galesville MD
7:00pm – Rock Steady Band – Town Hall Concert Series – La Plata MD
7:00pm – Joe Matthews Band – The Potomac Gardens – Colton’s Point MD
7:30pm – John Luskey – Killarney House Irish Pub – Davidsonville MD
8:00pm – Mariah Jean – The Scuttlebutt – Cobb Island MD
8:00pm – Smoke Signals – Toots Bar – Hollywood MD
Saturday – May 30th
11:30am – Ryan Forrester – The Boathouse @ Anchored Inn – Deale MD
12:00pm – Bryan Frates Band – Running Hare Winery – Prince Frederick MD
12:00pm – Vince Borelli – Two Lions Vineyards – Brandywine MD
1:00pm – Joseph Norris – Xella Winery – Mechanicsville MD
1:00pm – Shaun Gomban – Ketch 22 Restaurant – North Beach MD
1:00pm – Midnight Sunsets – Creekside Farm Brewery – King George VA
2:00pm – David Sparrow – Port of Leonardtown Winery – Leonardtown MD
2:00pm – Mike Mead – Robin Hill Farm & Vineyards – Brandywine MD
2:00pm – Alex Barnett – Corteau Vineyards – Mechanicsville MD
2:00pm – HydraFX – The Boathouse @ Anchored Inn – Deale MD
3:00pm – Rik Ferrel – Skipper’s Pier – Deale MD
3:00pm – Suzy & Shaun – Pirate’s Cove Dock Bar – Galesville MD
4:30pm – Sister Midnight – The Boathouse @ Anchored Inn – Deale MD
5:00pm – Even Ross – Happy Harbor Restaurant – Deale ND
6:00pm – Joe Cox – Running Hare Vineyard – Prince Frederick MD
6:00pm – Dead Eye Stare – Seabreeze Tiki Bar – Mechanicsville MD
6:00pm – Copper Pennies – Southern Trail Distillery – Mechanicsville MD
6:00pm – The New Normal – The TIKI Bar – Solomons MD
6:00pm – Shaun Gomban – Stoney’s Clarkes Landing – Hollywood MD
6:00pm – Carla Simpson – The Local – Hollywood MD
6:00pm – Kevin Howard Jazz – Corteau Vineyards – Mechanicsville MD
6:00pm – Girl Crush – The Pier House – Newburg MD
6:00pm – John Luskey – Dockside Restaurant & Sports Bar – Deale MD
6:30pm – Monkey Business – Bugeye Grill – Solomons MD
6:30pm – Funkzilla – Bluefish Pub – Solomons MD
7:00pm – Wes Ryce – Cypress Roots Brewing Co. – Pocomoke City MD
7:00pm – The Fabulous Hubcaps – Rod ‘N’ Reel – Chesapeake Beach MD
7:00pm – Shaun Mussleman – Pirate’s Cove Dock Bar – Galesville MD
7:00pm – All Funked Up Experience – The Scuttlebutt – Cobb Island MD
7:00pm – Joey Tippett – The Brass Tap – California MD
7:00pm – Latrice Carr – Pier 450 Restaurant – Ridge MD
7:00pm – Brooke Foster – Neptune’s Seafood Pub – North Beach MD
7:00pm – Smoke Signals – Dockside Tiki Bar – Colonial Beach VA
7:00pm – Billy Breslin – Wildewood Community Center – California MD
8:00pm – Linwood Taylor & Still Standing – Buckets Bar & Grill – Lusby MD
8:00pm – Never 2 Late – Cryer’s Back Road Inn – Leonardtown MD
8:00pm – Sundown – Toots Bar – Hollywood MD
9:00pm – Myles Deep Band – 219 Restaurant – Alexandria VA
9:00pm – Chris Dean & Matt Silkworth – Huntt’s Tavern – Pomfret MD
9:00pm – Thunderball – Apehangers Bar & Grill – Bel Alton MD
Sunday – May 31st
1:00pm – Justin Singleton – Running Hare Winery – Prince Frederick MD
2:00pm – Greg Barrick – Skipper’s Pier – Deale MD
2:00pm – Nightcap Trio – The TIKI Bar – Solomons MD
2:00pm – SVV Duo – Pirate’s Cove Dock Bar – Galesville MD
2:00pm – Stars in Bars – Seabreeze Tiki Bar – Mechanicsville MD
2:00pm – South Creek – Apehangers Bar & Grill – Bel Alton MD
2:00pm – Swamp Weasels – Port of Leonardtown Winery – Leonardtown MD
2:00pm – Eddie Anderson – Robin Hill Farm & Vineyards – Brandywine MD
2:00pm – Just Us – Wharf 38 – Deale MD
3:00pm – Bryan Frates Band – Dockside Restaurant & Sports Bar – Deale MD
3:00pm – Kiara Vos – Toots Bar – Hollywood MD
3:00pm – Chris Dean – The Pier River Bar – Solomons MD
3:00pm – Midnight Sunsets – The Boathouse @ Anchored Inn – Deale MD
4:00pm – Arkansas Williams – Happy Harbor Restaurant – Deale ND
5:30pm – Funkzilla Unplugged – Bugeye Grill – Solomons MD
6:00pm – Kurt Gibbons – Pirate’s Cove Dock Bar – Galesville MD
Monday – June 1st
Tuesday – June 2nd
7:00pm – Open Mic w/Derek Norris – Twisted Bar & Grill – Hollywood MD
Wednesday – June 3rd
12:00pm – Hump Day Band – Cryer’s Back Road Inn – Leonardtown MD
5:00pm – Madisun Bailey – 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
7:00pm – Open Mic w/Steve Nelson – The Tavern – Saint Leonard MD
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