SOUTHERN MARYLAND – Father’s Day weekend is packed with ways to celebrate dad—from crab feasts to classic car shows and family festivals. Add in Juneteenth events, art shows, and local markets, and Southern Maryland is full of culture, creativity, and community pride. This week’s roundup across Calvert, Charles, and St. Mary’s counties includes live music, hands-on history, and plenty of family fun. Whether you’re into food, music, history, or hands-on fun—it’s all here.

View our full roundup for Father’s Day Events here: Father’s Day Events in Southern Maryland Happening This Weekend

To have your upcoming event featured, please enter your event information on our Events Calendar. 

Food Truck Fridays at Annmarie on June 13 (5:00 p.m. to 7 p.m.), located at Annmarie Sculpture Garden and Arts Center, 13470 Dowell Road, Solomons, MD – Join us at Annmarie Sculpture Garden & Arts Center for extended hours! A food truck will be on site to serve you, as you wander our beautiful gardens and marvel at awe-inspiring sculptures and works of art.

Poker Run on June 14 (9:00 a.m. to 3:30 p.m.), located at Traders Chesapeake, 8132 Bayside Rd, Chesapeake Beach, MD – Start and finish at Traders Chesapeake for this charitable ride benefiting the Humane Society of Calvert County. First bike out at 11 a.m., with trophy awards for best and worst poker hands. $20 per hand; $10 each additional hand.

End Hunger Dragon Boat Festival on June 14 (9:00 a.m. to 4:00 p.m.), located at Town of North Beach, 8916 Chesapeake Avenue, North Beach, MD 20714 – Teams of paddlers and drummers race long boats across the bay in a spirited competition to raise awareness and funds for End Hunger in Calvert County. Family-friendly event with food, music, and waterfront fun. Free admission for spectators; donations encouraged.

Youth Market on June 14 (9:00 a.m. to 2:00 p.m.), located at Annmarie Sculpture Garden & Arts Center, 13470 Dowell Rd, Solomons, MD – Youth entrepreneurs aged 7–22 showcase handmade art and products. Free admission.

Father’s Day Evening Cruise on June 15 (4:30 p.m. to 6:00 p.m.), located at Calvert Marine Museum, 14200 Solomons Island Road, Solomons, MD 20688 – Celebrate Father’s Day with a scenic evening cruise featuring heavy hors d’oeuvres, dessert, and refreshments. Guests may bring additional food and alcoholic beverages (21+). $40 for ages 13+; $20 for ages 5–12; $15 for ages 4 and under. Registration required.

Planned Giving Educational Seminar on June 18 (6:30 p.m.), located at Annmarie Sculpture Garden & Art Center, 13470 Dowell Road, Dowell, MD – Learn about planned giving strategies at this free seminar hosted by Ann’s Circle and presented by Wells Fargo. The evening includes a financial presentation, a Q&A session, and light refreshments. Free admission.

Painting with Primitive Pigments Workshop on June 18 (6:30 p.m. to 8:30 p.m.), located at Jefferson Patterson Park & Museum, 10515 Mackall Road, St. Leonard, MD 20685 – A hands-on art session exploring historic painting techniques and natural pigments, tailored for participants aged 9 and up. Free admission; drop-in welcome. 

Teacher Appreciation Cruise on June 19 (3:45 p.m. and 6:30 p.m.), located at Big Kahuna Cruises, 14426 Solomons Island Rd S, Solomons, MD – Recognizing educators with a scenic cruise. Tickets required. 

Rock the Dock: All‑Star Purple Party (Prince Tribute) on June 19 (7:00 p.m. to 10:00 p.m.), located at The Bandshell at Rod ’N’ Reel Resort, Chesapeake Beach, MD – Live music tribute to Prince. Ticket required.

For more Calvert County events, visit the Calvert County Maryland website. 

90s R&B Sing-Along: Date Night Workshop on June 13 (multiple times), located at Gia Candle Bar, 11110 Mall Circle, Waldorf, MD – A romantic hands-on workshop where couples create custom massage oils and love candles to the sounds of 90s slow jams. Tickets required.

Community Art Day on June 14 (7:00 a.m. to 3:00 p.m.), located at Elite Gymnastics and Recreation Center, 2745 Old Washington Road, Waldorf, MD – A hands-on collaborative mural-painting event led by local artist Donald Ely. Supplies provided, with games and refreshments throughout the day. RSVP by emailing BlessingA@charlescountymd.gov. Free; RSVP required. 

Shops at Waldorf Center Classics Car Show on June 14 (10 a.m. to 3 p.m.), located at The Shops at Waldorf Center, 2952 Festival Way, Waldorf, MD – Join DMV Rod’s & Classic’s Car Club for another exciting showcase of classic cars! Enjoy live music, raffles, food vendors, and a chance to win one of 100 trophies. All cars welcome. Free admission. 

JCPenney Kids Zone on June 14 (11:00 a.m. to 12:00 p.m.), located at JCPenney, 11130 Mall Cir, Waldorf, MD 20603 – Free Father’s Day craft where kids create a taco keychain and card, receive an ID badge, lanyard, collector’s pin; parents get a 10% off in-store coupon valid that day. Free; no registration needed.

Cobb Island Day on June 14 (11:00 a.m. to 4:00 p.m.), located at Fisherman’s Field, Cobb Island, MD – A full day of family fun kicks off with a hometown parade at 11:00 a.m.. Enjoy all-day attractions including the Circus City Triple Lane Bounce Park, a 9-hole mini-golf course, a rock wall with the Extreme Sky Flyer, food, carnival games, music, and more. The event also features a silent auction, 50/50 raffle, live demonstrations, and dozens of local crafters and vendors.Free admission.

Moonlight Movie Nights on June 14 (at dusk), located at The Shops at Waldorf Center, 2952 Festival Way, Waldorf, MD – Enjoy a free family-friendly movie under the stars on the second Saturday of the month. Bring a blanket or lawn chair and settle in for a fun evening outdoors. Free admission. Rain date: June 21.

Charles County NAACP ACT-SO Showcase on June 14 (11:00 a.m. to 1:00 p.m.), located at The Space by LBI Collective, 2901 Festival Way, Waldorf, MD 20601 – Celebrate and support local ACT-SO gold medalists as they prepare to represent Charles County at the national NAACP competition in Charlotte, NC. The event highlights excellence in the arts, STEM, and humanities through student performances and presentations. Free admission; donations welcome.

Father’s Day Game – Southern Maryland Blue Crabs on June 15 (2:05 p.m.), located at Regency Furniture Stadium, 11765 St Linus Dr, Waldorf, MD – Celebrate Father’s Day with minor league baseball, stadium snacks, and family fun as the Blue Crabs take the field. Ticket purchase required.

Celebrate Juneteenth: Community Mural Project on June 16 (10:00 a.m. to 11:00 a.m.), located at La Plata Branch, 2 Garrett Avenue, La Plata, MD – Join CCPL for the second annual community mural creation in honor of Juneteenth. Add your own artistic touch to a collective display celebrating freedom, resilience, and Black history. Free; no registration required.

3rd Annual Celebration of Freedom & the Arts (Juneteenth) on June 19 (2:00 p.m. to 5:30 p.m.), located at Village Green, 100 Walter Thomas Rd, Indian Head, MD – A cultural celebration featuring live performances, community arts, and historical reflection in honor of Juneteenth. Free admission.

For more Charles County events, visit the Charles County Maryland website. 

Mr. Jon Concert with St. Mary’s Library on June 13–14 (various times and libraries) – Enjoy a lively and sensory-friendly performance with Mr. Jon and George the Monkey, featuring music, laughter, and interactive fun for all ages—especially children with sensory sensitivities. Free; no registration required.

Storytime in the Park (LTown Alley) on June 13 (6:00 p.m.), located at LTown Alley Parkette, 22698 Washington St, Leonardtown, MD – Bring the kids for an outdoor reading of The Tale of Peter Rabbit by Beatrix Potter, plus crafts, face painting, giveaways, and more in a welcoming, family-friendly setting. Hosted by the Town of Leonardtown and Fenwick Street Used Books. Free admission.

Lavender Days Festival on June 14–15 (11:00 a.m. to 6:00 p.m.), located at Dixon Family Farm, 27075 South Sandgates Road, Mechanicsville, MD – Celebrate summer among blooming lavender fields with live music, food trucks, local craft vendors, distillation demonstrations, and scenic waterfront views. Sunday includes a kids’ petting zoo and face painting. Tickets: $12–$18; free for ages 3 and under. More info & tickets.

The Fabulous Hubcaps at the St. Mary’s County Crab Festival on June 14 (12 p.m. to 6 p.m.), located at St. Mary’s County Fairgrounds, 42455 Fairgrounds Rd, Leonardtown, MD – Enjoy a day of live music from The Fabulous Hubcaps, hot crabs, cold beer, arts & crafts, food trucks, and a classic car show. Tickets required ($10 entry; free for ages 12 and under).

Nature Walk & Talk at Summerseat Farm on June 14 (9:00 a.m. to 11:00 a.m.), located at Summerseat Farm, 26655 Three Notch Rd, Mechanicsville, MD – Explore the newly revitalized Discovery Trail during a guided walk led by Maryland Master Naturalist Bill Cheeseman. This leisurely nature walk includes open discussion on local flora and fauna. Great for curious minds of all ages. Free admission; meet inside the main entrance.

Coastal Arts Market on June 14 (10:00 a.m. to 3:00 p.m.), located at Leonardtown Wharf, 22500 Washington Street, Leonardtown, MD 20650 – A seasonal waterfront market offering handmade goods from local artisans, including art, jewelry, treats for pets and people, and more. Enjoy a picnic in the park or grab a bite in Leonardtown Square after shopping. Free admission.

Flag Day Celebration on June 14 (6:00 p.m. to 7:00 p.m.), located at St. Mary’s County Governmental Center Lawn, 41770 Baldridge St, Leonardtown, MD 20653 – A patriotic community event featuring a procession of color guards and veteran groups, a formal Flag Day service, and a Flag Retirement Ceremony. Includes food, music, handheld American flags, and kids’ activities. Free admission. In case of rain, the event moves indoors to Leonard Hall Recreation Center.

SMTMD Contra Dance on June 14 (7:00 p.m. to 9:30 p.m.), located at Christ Episcopal Church Parish Hall, 37497 Zach Fowler Road, Chaptico, MD – The evening starts at 7  p.m. with a half hour beginner’s dance workshop followed by live music performed by the SOMD Open Band and dancing from 7:30 to 9:30  p.m.. Check the website calendar for the lineup of dances and callers. Admission: $8 for members; $12 for non‐SMTMD members; children 17 and under (when accompanied by a paying adult) and band members are free.

JCPenney Kids Zone on June 14 (11:00 a.m. to 12:00 p.m.), located at JCPenney, 23415 Three Notch Rd, California, MD 20619 – Same free crafts and giveaways: taco keychain/card, ID badge, lanyard, collector’s pin; parents receive a 10% off one-day coupon. Free; walk-in welcome.

Classic & Antique Car Show at the St. Mary’s County Crab Festival on June 14 (11 a.m. to 3 p.m.), located at St. Mary’s County Fairgrounds, 42455 Fairgrounds Rd, Leonardtown, MD – Show off your ride or admire classic and antique vehicles during this judged show featuring trophies, plaques, and dash plates. Registration closes at noon; awards announced at 3  p.m.. Pre-registration is $15 (includes driver admission); $20 at the gate. For entry forms, email payneml@md.metrocast.net.

For more St. Mary’s County events, check out the Visit St. Mary’s MD website. 

Saturday – June 14th
10:00am – Byron Ciotter – Bugeye Grill – Solomons MD
11:00am – GrooveSpan – Lavender Days @ Dixon Farm – Mechanicsville MD
12:00pm – The Hubcaps – Crab Fest @ SMC Fairgrounds – Leonardtown MD
12:30pm – Elena Barrett Duo – Running Hare Winery – Prince Frederick MD
1:00pm – Cole Larravide – Xella Winery & Vineyard – Laurel Grove MD
2:00pm – Dust on the Bottle – Corteau Vineyards – Mechanicsville MD
2:00pm – Monkey Business – Port of Leonardtown Winery – Leonardtown MD
2:00pm – High Energy Caribbean Band – Robin Hill Farm – Brandywine MD
3:00pm – Steve Potter Band – ArtsFest @ Village Green – Indian Head MD
3:00pm – On Bleeker St. – Lavender Days @ Dixon Farm – Mechanicsville MD
3:00pm – Greg Barrick – The Boathouse @ Anchored Inn – Deale MD
4:00pm – Thunderball – Crab Fest @ SMC Fairgrounds – Leonardtown MD
5:00pm – Fat Whiskey – Happy Harbor Restaurant – Deale MD
5:00pm – Joseph Norris – Morris Point Restaurant – Abell MD
5:00pm – Sister Midnight – Coconuts Tiki Bar – Ocean City MD
5:30pm – Jack Allen – Maltese Brewing – Fredericksburg VA
5:30pm – Mike Mead & Eric Wolf – Running Hare – Prince Frederick MD
6:00pm – Doc Lohn – The Local – Hollywood MD ????
6:00pm – Jason Bishop – Dockside Restaurant & Sports Bar – Deale MD
6:00pm – Suckerpunch – Wheel House Beer Garden – North Beach MD
6:00pm – Country Memories – Blue Fish Pub – Solomons MD
6:00pm – Screaming Monkeys – The TIKI Bar – Solomons MD
6:00pm – Motorboat Co. – Southern Trail Distillery – Mechanicsville MD
6:00pm – Dagenhart – Seabreeze Tiki Bar – Mechanicsville MD
6:25pm – Nelson, Cheseldine & Starnes – Atomic Seafood- Lusby MD
7:00pm – Social – High Tides on the Potomac – Colonial Beach VA
7:00pm – Hyland Brothers – Pirates Cove Dock Bar – Galesville MD
7:00pm – Joe Bernui – Babes Boys Tavern – Waldorf MD
7:00pm – GypsySol – Pax River Ale House – Lexington Park MD ????
7:00pm – Nightcap – 6 Bears & A Goat Brewery – Fredericksburg VA
7:00pm – Byron Ciotter – The Brass Tap – California MD
8:00pm – Fast Eddie & the Boys – Gridiron Grill – Callaway MD ????
8:00pm – Wesley Spangler – The Tavern – Saint Leonard MD
8:00pm – Drivetrain – Buckets Bar & Grill – Lusby MD
8:00pm – Fake Happy (Paramore tribute) – Rex Theatre – Leonardtown MD
8:00pm – Copper Pennies – Toots Bar – Hollywood MD
9:00pm – Hate The Toy – Apehangers Bar & Grill – Bel Alton MD

Sunday – June 15th
11:00pm – Rob Blake – Dockside Tiki Bar – Colonial Beach VA
11:00am – On Bleeker St – Lavender Days @ Dixon Farm – Mechanicsville MD
2:00pm – The Bootleggers – Port of Leonardtown Winery – Leonardtown MD
2:00pm – Hyland Brothers – Traders Seafood & Ale – Chesapeake Beach MD
2:00pm – Drivetrain – Seabreeze Tiki Bar – Mechanicsville MD
2:00pm – Marianne Styles – Robin Hill Farm & Vineyards – Brandywine MD
2:00pm – Pete Best – Wharf 38 – Deale MD
2:00pm – Bay Country – Southern Trail Distillery – Mechanicsville MD
3:00pm – Mele Nahenahe – Wheel House Beer Garden – North Beach MD
3:00pm – Vicki Roberts Band – Dockside Restaurant & Sports Bar – Deale MD
3:00pm – Kevin Lee – Lavender Days @ Dixon Farm – Mechanicsville MD
3:00pm – Ryan Keith Band – The Boathouse @ Anchored Inn – Deale MD
3:00pm – Jack Allen – The Pier – Solomons MD
3:00pm – Midnight Sunsets – The TIKI Bar – Solomons MD
3:00pm – Whiskey Brothers – Happy Harbor Restaurant – Deale MD

Monday – June 16th
7:00pm – Open Mic w/ Will Benthal – Toots Bar – Hollywood MD

Tuesday – June 17th
6:30pm – Open Mic w/Mike Trujillo – Twisted Bar & Grill – Hollywood MD

Wednesday – June 18th
5:00pm – John Luskey – The Boathouse @ Anchored Inn – Deale MD
6:00pm – Greg Barrick – The Pier – Solomons MD
6:00pm – – Brick Wood Fired Bistro – Prince Frederick MD
7:00pm – Open Mic w/Steve Nelson – The Tavern – Saint Leonard MD

Contact our news desk at news@thebaynet.com