SOUTHERN MARYLAND — Summer may be winding down, but Southern Maryland’s calendar is still packed with reasons to get out of the house.
This week brings live music, family activities, festivals, art, games and nights out across Calvert, Charles and St. Mary’s counties. Toot’s Bar keeps the fun rolling in Hollywood, including its Family Funday Luau on Sunday, while kids can get creative during St. Clement’s Island Museum Art Kids. Gospel music takes center stage Saturday at the Alice G. Brooks Memorial Gospel Fest, and there is still time to grab tickets to see Brothers Osborne at the Calvert Marine Museum’s Waterside Music Series Saturday night.
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 Concert Guide for Southern Maryland here.
🍦 See where Kids Eat Free in Southern Maryland here.
Turtle Time at North Beach Nature Center on Fri. Aug. 21 (11 a.m.–noon), at North Beach Nature Center, 9404 Dayton Avenue, North Beach, MD – A turtly-awesome program for young nature lovers ages Pre-K through 5th grade — storytime, turtle artifacts, a craft and a meet-and-greet with three ambassador turtles while learning to identify different turtle species. Free admission.
Summer Night Festival on Fri. Aug. 21 (6–8 p.m.), at Kellam’s Field Complex, 3825 Gordon Stinnett Avenue, Chesapeake Beach, MD – A warm summer evening of live music, local vendors and community connection at this ongoing seasonal series — a relaxed, welcoming outdoor gathering for residents and visitors of all ages. Contact 410-257-2230 for details. Free admission.
Bad Art Night at Annmarie Garden on Fri. Aug. 21 (5–8 p.m.), at Annmarie Sculpture Garden & Arts Center, 13470 Dowell Road, Solomons, MD – An outrageous adults-only evening of unconventional artmaking inspired by the gallery works — all supplies provided, completed pieces go on display and guests vote for the Best of the Worst. Entertainment, a cash bar and a food truck round out the night. Ages 21 and over. No reservations required. Ticket required.
Dried Flower Shadow Box Workshop at WhataBoba on Fri. Aug. 21 (6–8 p.m.), at WhataBoba, 232 Town Square Drive, Lusby, MD – Create a beautiful custom dried flower shadow box — choose a 5×5 or 5×7 size, with all supplies and instruction included. You’re welcome to bring your own dried flowers. Sample a tea or freeze-dried candy during the workshop. Ticket required.
10th Annual Solomons Dragon Boat Festival on Sat. Aug. 22 (races begin 9 a.m.), at Patuxent River, Solomons, MD – The centerpiece event of the summer returns for its 10th anniversary — up to 30 teams of paddlers compete for glory on the Patuxent River in a full day of dragon boat races, an opening ceremony, children’s activities, a vendor village and an awards ceremony. Free admission.
Baia Run Club — 1st Anniversary Morning Run on Sat. Aug. 22 (9:30 a.m.), at Baia Coastal Italian Kitchen & Wine Bar, 8323 Bayside Road, Chesapeake Beach, MD – Celebrate one year of running the coast with the Baia Run Club’s anniversary social run along the Chesapeake Bay — all paces welcome, with a well-earned drink waiting at Baia when you’re done. The morning run meets the 4th Saturday of every month at 9:30 a.m. Free admission.
Guided Canoe Trip at Parkers Creek on Sat. Aug. 22 (10 a.m.–1 p.m.), at Parkers Creek, Port Republic, MD – Paddle up one of the most protected creeks on the western shore of the Chesapeake Bay with expert ACLT guides through the 3,200-acre Parkers Creek Preserve — canoes provided for two-person teams or bring your own canoe or kayak. Physically strenuous; not recommended for inexperienced paddlers. Children 5 and under and pets not permitted. Ticket required.
Alice G. Brooks Memorial Gospel Fest 2026 — on Sat. Aug. 22 (3 p.m.), at Calvert County Fairgrounds, 140 Calvert Fair Drive, Prince Frederick, MD — Celebrate gospel music and community at the annual Alice G. Brooks Memorial Gospel Fest, featuring an afternoon of uplifting live performances. Ticket required.
Brothers Osborne — Waterside Music Series on Sat. Aug. 22, at Motto Mortgage Preferred and RE/MAX One Waterside Pavilion at Calvert Marine Museum, 14200 Solomons Island Road, Solomons, MD – The genre-blending duo celebrates the 10-year anniversary of their breakthrough album Pawn Shop in a high-energy performance at one of Southern Maryland’s most scenic waterfront venues — one of the marquee concerts of the 2026 Waterside Music Series season. Tickets available through Etix. Ticket required.
Sunset Splash at NRC Solomons on Sat. Aug. 22 (7–9 p.m.), at Riverside Pool, NRC Solomons, 13855 Solomons Island Road, Solomons, MD – Take a dip at the Riverside Pool on select summer evenings for this after-hours splash event — a fun way to cool down as the day winds down. Open to all with base access. Free admission.
Movies on the Beach: Lilo & Stitch on Sat. Aug. 22 (dusk), at North Beach Town Beach, North Beach, MD – Bring your beach chair or blanket and settle in for a free outdoor movie projected on a large inflatable screen in the sand — a beloved community tradition open to all. Free admission.
Endless Summer Wine Tasting at No Thyme to Cook on Sun. Aug. 23 (noon–4 p.m.), at No Thyme to Cook, 14624 Solomons Island Road S., Solomons, MD – Join Chef Gwyn Novak for a curated Sip & Shop wine tasting celebrating the final stretch of summer — five 1-ounce pours hand-selected by Chef Gwyn, with special bottle savings available and waterfront shopping throughout the afternoon. Ticket required.
Trivia on Tap at Mully’s Taproom on Wed. Aug. 26 (6:30–8 p.m.), at Mully’s Taproom, 141 Schooner Lane, Prince Frederick, MD – Grab your crew, order a round and put your knowledge to the test at Mully’s weekly trivia night. Free admission.
Little Minnows: Amazing Amphibians on Thu. Aug. 27 (10:15 and 11:15 a.m.), at Calvert Marine Museum, 14200 Solomons Island Road, Solomons, MD – A hands-on early childhood program for children 18 months to 3 years with an adult, exploring the Amazing Amphibians theme through music, stories and special activities. Sign up at the Admissions Desk upon arrival. Ticket required for admission.
For more Calvert County events, visit the Calvert County Maryland website.
THINGS TO DO IN CHARLES COUNTY
☀️ See our Summer Concert Guide for Southern Maryland here.
🍦 See where Kids Eat Free in Southern Maryland here.
10 & Tea Cycling Chill Ride on Fri. Aug. 21 (meet 9:30 a.m., roll out 10 a.m.), at Clarity Coffee Shop, 4175 Indian Head Highway, Indian Head, MD – One of the last summer Friday morning community rides — all paces welcome for fresh air, good company and coffee before the season winds down. Free admission.
Friday Night Magic at RallyPoint Games on Fri. Aug. 21, at RallyPoint Games, 8132 Old Leonardtown Road, Hughesville, MD – Weekly Friday Night Magic: The Gathering events plus open play for board games and trading cards — all skill levels welcome. Free admission.
Summer Friday Special at Southern Maryland Paintball on Fri. Aug. 21(noon–5 p.m.), at Southern Maryland Paintball, 11272 Edge Hill Road, Newburg, MD – All-day paintball available every Friday through end of August — rental marker, rental mask, 400 paintballs and all-day play. Ticket required.
A Night of Miracles – Bears of Love & The Greater Waldorf Jaycees on Fri. Aug. 21 (5:30 p.m.-11 p.m.), at 3090 Crain Highway, Waldorf, MD – An evening fundraiser featuring an auction preview, dinner and music, with proceeds supporting the purchase of a NICU jet ventilator, breathing support for fragile newborns and DIPG research at Children’s National in memory of Finn Cusick. Ticket required.
Kaiser Permanente Presents: Health and Wellness Expo on Sat. Aug. 22 (9 a.m.-1 p.m.), at College of Southern Maryland Velocity Center, 4465 Indian Head Highway, Indian Head, MD – Enjoy breakout sessions, exhibitor tables, hands-on activities and wellness resources focused on improving quality of life in Charles County. Free admission. Registration required.
Raise a Glass: Il Gusto Ristorante 4th Anniversary Celebration on Sat. Aug. 22, at Il Gusto Ristorante, 230 Rosewick Road, La Plata, MD – Celebrate four years of authentic Italian flavors and warm Southern Maryland hospitality with the Il Gusto team — reservations encouraged. Contact the restaurant directly to reserve your seat. Free admission.
Back to School Community Day on Sat. Aug. 22 (11 a.m.-2 p.m.), at The All American Steakhouse Waldorf, 35 St. Patrick’s Drive, Waldorf, MD – A back-to-school community event featuring free school supplies, clothing, cleaning and hygiene supplies, shelf-stable food, children’s books, toiletries and other resources for families while supplies last. Free admission.
Iron Angels – Ladies Night at All American Harley on Sat. Aug. 22 (5:30-8 p.m.), at All American Harley-Davidson, 8126 Old Leonardtown Road, Hughesville, MD – A ladies night featuring informational stations, a scavenger hunt, light refreshments and opportunities to learn more about bikes, parts, gear and maintenance while connecting with fellow riders. Free admission. Registration required.
Casting for a Cure on Sat. Aug. 23 (6 a.m.-1 p.m.), at The Brick House Cove Marina, 16320 Cobb Island Road, Newburg, MD – A white perch fishing tournament held in memory of Peyton Greer, with a 50-50 raffle, silent auctions, T-shirts, wristbands and music by Todd Good. Proceeds will benefit Children’s National Hospital for cancer research and Clement’s Cuties Foundation to support local children battling cancer. Registration and payment required for tournament participants.
Mallows Bay Park on select days this week, at Mallows Bay Park, 1440 Wilson Landing Road, Nanjemoy, MD – Home to the world’s largest ghost fleet of sunken WWI-era wooden steamships, Mallows Bay offers kayak and canoe access amid a thriving wildlife habitat — a one-of-a-kind outdoor experience in southern Charles County. Free admission.
Court Programs Drop-In Sessions at Capital Clubhouse, 3033 Waldorf Market Place, Waldorf — soccer, volleyball and basketball drop-in sessions plus clinics and camps for all ages, running throughout the week. Tickets required.
For more Charles County events, visit the Charles County Maryland website.
THINGS TO DO IN ST. MARY’S COUNTY
☀️ See our Summer Concert Guide for Southern Maryland here.
🍦 See where Kids Eat Free in Southern Maryland here
Weekly Fun at Toot’s Bar Aug. 21–27, at Toot’s Bar, 23971 Mervell Dean Road, Hollywood, MD – Dead Eye Stare kicks off the weekend Friday Aug. 21 (doors 4 p.m.), FADE TO BLACK! rocks Saturday Aug. 22 ($5 cover, doors 4 p.m.) and Sunday Aug. 23 brings the Family Funday Luau for a tropical day of fun. Barstool Bingo returns Tuesday and Corn Hole League and Beer Pong wrap the week Thursday.
Shakespeare’s Macbeth at The Newtowne Players Theater — from Aug. 21-23 (7 p.m. Thursday; 8 p.m. Friday-Saturday; 3 p.m. Sunday), at The Newtowne Players Theater, 21744 South Coral Drive, Lexington Park, MD — Shakespeare’s tragedy is reimagined in the Jazz Era, with smoky nightclubs, mysterious singers and a ruthless pursuit of power. Ticket required.
Sportsmen’s Bash on Sat. Aug. 22 (9 a.m.), at Seventh District Volunteer Fire Department, 21660 Colton Point Road, Brandywine, MD – A community sportsmen’s bash hosted by the Seventh District Volunteer Fire Department featuring raffle items and prizes. Ticket required.
Pro Motocross Championship — Yamaha Budds Creek National on Sat. Aug. 22 (opening ceremonies noon), at Budds Creek Motocross Park, 27963 Budds Creek Road, Mechanicsville, MD – Round 10 of the prestigious Pro Motocross Championship sanctioned by AMA Pro Racing comes to Southern Maryland with championship battles coming down to the wire. Ticket required.
Race for Life & Strider Cup at SOMD BMX Racetrack on Sat. Aug. 22 (5–10 p.m.), at SOMD BMX Racetrack at Chaptico Park, 26600 Budds Creek Road, Mechanicsville, MD – A one-day, three-event race for all ages — a Strider Cup for ages 1–5, a memorial race for ages 3–99 on pedal bikes and a kids movie on the jumbotron to close out the night. Free admission.
Women’s Conference Weekend on Sat. Aug. 22 through Sun. Aug. 23, at First Missionary Baptist Church, 46370 Pegg Lane, Lexington Park, MD – The 2026 Women’s Conference Weekend Celebration presented by the Women’s Ministry — themed Women of God: Consistent, Committed and Courageous. Contact the church directly for schedule and registration details. Free admission.
Sunrise Yoga at the Wharf on Sun. Aug. 23 (7:30–8:30 a.m.), at Leonardtown Wharf, Leonardtown, MD – Start Sunday morning with peaceful movement and waterfront views at the Wharf — presented by SPICE Studio, with class credits applying. Sign up through the Mindbody app or at spicestudio.com. Ticket required.
Cars & Coffee Car Show at The Bell Building on Sun. Aug. 23 (10 a.m.–2 p.m.), at The Bell Building, 22675 Washington Street, Leonardtown, MD – The biweekly Sunday car show in historic downtown Leonardtown with amazing rides, a 50/50 raffle, door prizes, corn hole and live music. Free admission.
St. Clement’s Island Museum Art Kids (SCIMAK) — from Aug. 24-27 (6 a.m.), located at St. Clement’s Island Museum, 38370 Point Breeze Road, Coltons Point, MD — Children ages 7-14 can explore painting, drawing, weaving, sculpting and other hands-on art projects while creating their own artwork to take home. Cost is $7 per child and all materials are provided. Registration required.
Ladies Night at Swords & Spoons on Mon. Aug. 24 (6 p.m.), at Swords & Spoons, 22599 MacArthur Blvd., California, MD – A welcoming, inclusive evening celebrating women in tabletop gaming — bring your favorite game or discover something new, with trading card games, board games, roleplaying, miniatures, social deduction and more. Come solo or bring your crew. Free admission.
Trivia Night at Brudergarten Beer Garden on Wed. Aug. 26 (7–9:30 p.m.), at Brudergarten Beer Garden, 22725 Duke Street, Leonardtown, MD – Put your knowledge to the test every Wednesday night at this indoor/outdoor beer garden featuring 20 taps, domestic and foreign beers and craft cocktails. Free admission.
Homeschool Share Fair at Patuxent River Youth Center on Thu. Aug. 27 (11 a.m.–12:30 p.m.), at Patuxent River Youth Center, NAS Patuxent River, Lexington Park, MD – The NAS Patuxent River School Liaison invites homeschool families to a special sharing event connecting them with curriculum resources, local organizations and fellow homeschool families. Open to all with base access. Contact 202-330-3093. Free admission.
Game Show Night: Wheel of Fortune — on Thu. Aug. 27 (1:30 p.m.) at Garvey Senior Activity Center, 23630 Hayden Farm Lane, Leonardtown, MD; enjoy a Wheel of Fortune-style game show afternoon at the senior activity center.
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 – August 21st
5:00pm – Karlee Ryce – Greene Turtle Sports Bar – California MD
5:00pm – Cole Larravide – Mully’s Brewery – Prince Frederick MD
6:00pm – Lynn Drury – Helen’s Cafe – Leonardtown MD
6:00pm – Byron Ciotter – Riverboat on the Potomac – Colonial Beach VA
6:00pm – Jason Bishop – Stoney’s Clarkes Landing – Hollywood MD
6:00pm – Jack McNutt – The Local – Hollywood MD
6:00pm – Sam Grow / Hyland Brothers – Running Hare – Prince Frederick MD
6:00pm – Billy Breslin – Angler’s Seafood Bar & Grill – Solomons MD
6:00pm – Girl Crush – The Pier House – Newburg MD
6:00pm – Mixed Business – Wheel House Beer Garden – North Beach MD
6:00pm – Joe Cox – Seabreeze Tiki Bar – Mechanicsville MD
6:00pm – Greg Barrick – Dockside Restaurant & Sports Bar – Deale MD
6:00pm – Hat Trick Band – Blue Fish Pub – Solomons MD
6:00pm – David Norris & Stu – Ruddy Duck Brewery & Grill – Solomons MD
6:00pm – Under The Covers – The TIKI Bar – Solomons MD
6:00pm – Doug Segree – Pirates Cove Dock Bar – Galesville MD
7:00pm – Coastal Country – Town Hall Concert Series – La Plata MD
7:00pm – Stapleton / Combs (tribute) – Rod ‘N’ Reel – Ches.Beach MD
7:30pm – Shaun Gomban – Drift Inn Crab House – Mechanicsville MD
8:00pm – Chris Dean – Bushmill Tavern – Abington MD
8:00pm – Dead Eye Stare – Toots Bar – Hollywood MD
9:00pm – Squid Inc – Twisted Bar & Grill – Hollywood MD
Saturday – August 22nd
1:00pm – Rock The Mountains – Allegany Fairgrounds – Cumberland MD
——— 1:10 – shallowDeep, 1:50 – Red Skies Dawning & Others –
1:00pm – Local Songwriter Showcase – JaneMark Winery – Brandywine MD
2:00pm – Madisun Bailey – Ketch 22 Restaurant – North Beach MD
2:00pm – Justin Crenshaw – Port of Leonardtown Winery – Leonardtown MD
2:00pm – California Bob – Perigeaux Winery – Saint Leonard MD
2:00pm – Dust on the Bottle – Corteau Vineyards – Mechanicsville MD
2:30pm – Nightcap – NOVA Live – Manassas VA
3:00pm – Kurt Gibbons – Pirates Cove Dock Bar – Galesville MD
3:00pm – Joe Cox – The Scuttlebutt – Cobb Island MD
3:00pm – Vicki Roberts Band – Skippers Pier – Deale MD
6:00pm – One Way Moe – Helen’s Cafe – Leonardtown MD
6:00pm – Loose Change – Wheel House Beer Garden – North Beach MD
5:00pm – John Luskey – The Pier House – Newburg MD
6:00pm – Justin Taylor – Port Tobacco Restaurant – Port Tobacco MD
6:00pm – Swamp Weasels – Southern Trail Distillery – Mechanicsville MD
6:00pm – Drivetrain – Traders Seafood & Ale – Chesapeake Beach MD
6:00pm – Chris Darlington – Blue Fish Pub – Solomons MD
6:00pm – Framing the Tin Man – Seabreeze Tiki Bar – Mechanicsville MD
6:00pm – Wes Ryce – Dockside Restaurant & Sports Bar – Deale MD
6:00pm – New Normal – The TIKI Bar – Solomons MD
6:00pm – Sean Postanowicz – Stoney’s Clarkes Landing – Hollywood MD
6:30pm – Monkey Business – Bugeye Grill – Solomons MD
7:00pm – SVV Duo – Pirates Cove Dock Bar – Galesville MD
7:00pm – WildGood Acoustic – Wildewood Community Center – California MD
7:00pm – In 2 Deep – The Taphouse 1637 – California MD
7:00pm – Greg Barrick – The Brass Tap – California MD
8:00pm – Changing Scene / Scale Models – The Tavern – Saint Leonard MD
8:00pm – South Creek – Cryer’s Back Road Inn – Leonardtown MD
8:00pm – Brothers Osborne – Calvert Marine Museum – Solomons MD
8:00pm – Never 2 Late – Buckets Bar & Grill – Lusby MD
8:00pm – Fade To Black (Metallica tribute) – Toots Bar – Hollywood MD
9:00pm – Midnight Sunsets – Apehangers Bar & Grill – Bel Alton MD
Sunday – August 23rd
1:00pm – John Luskey – Running Hare Winery – Prince Frederick MD
2:00pm – Greg Barrick – Wharf 38 – Deale MD
2:00pm – Matt Guilherme – Port of Leonardtown Winery – Leonardtown MD
2:00pm – Suzy & Shaun – Pirates Cove Dock Bar – Galesville MD
2:00pm – Hyland Brothers – Skipper’s Pier – Deale MD
2:00pm – Mike Newberry – The TIKI Bar – Solomons MD
2:00pm – Monkey Business – Seabreeze Tiki Bar – Mechanicsville MD
2:00pm – Billy Breslin – Trifecta Restaurant – Solomons MD
3:00pm – Jason Bishop – Dockside Restaurant & Sports Bar – Deale MD
3:00pm – Brooke Foster – Wheel House Beer Garden – North Beach MD
3:00pm – Joe Cox – The Scuttlebutt – Cobb Island MD
3:00pm – Water’s Edge Band – The Pier House – Newburg MD
3:00pm – Shaun Gomban – Toots Bar – Hollywood MD
3:00pm – Doc Lohn – Stoney’s Clarkes Landing – Hollywood MD
5:00pm – Drowning Pool / Saliva / shallowDeep – The Rex – Leonardtown MD
6:00pm – Eddie Rogers – Pirates Cove Dock Bar – Galesville MD
Monday – August 24th
2:00pm – Dance Hall Ghosts – Toots Bar – Hollywood MD
Tuesday – August 25th
6:00pm – Joe Cox – Apehangers Bar & Grill – Bel Alton MD
6:00pm – Byron Ciotter – Pirates Cove Dock Bar – Galesville MD
6:30pm – Greg Barrick – The Tavern – Saint Leonard MD
7:00pm – Open Mic w/Derek Norris – Twisted Bar & Grill – Hollywood MD
Wednesday – August 26th
12:00pm – Hump Day Band – Cryer’s Back Road Inn – Leonardtown MD
4:30pm – Run Catch Rain – No Thyme To Cook – Solomons MD
5:00pm – Just Us – The Boathouse @ Anchored Inn – Deale MD
5:00pm – Shaun Gomban – Trifecta Restaurant – Solomons MD
5:00pm – Hyland Brothers – Ketch 22 Restaurant – North Beach MD
6:00pm – Angie Miller – Pirates Cove Dock Bar – Galesville MD
6:00pm – Levi Stephens – Brick Wood Fired Bistro – Prince Frederick MD
7:00pm – Open Mic w/Steve Nelson – The Tavern – Saint Leonard MD
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