SOUTHERN MARYLAND — School is back in session across Southern Maryland, and now it is time to enjoy the weekend. Catch live music, bingo, karaoke and more during a full week of fun at Toot’s Bar, pick grapes straight from the vines during Amber View Vineyard’s 1st Annual “Pick Your Own Grapes” Event, or celebrate the new school year with games, giveaways and family activities at All Aboard Child Development Center’s Back To School Love Your Neighborhood Block Party.
The fun continues with jousting, classic car shows, outdoor movies, live music, community art, a crab walk and plenty more happening throughout Calvert, Charles and St. Mary’s counties. Check out the full list and start planning your weekend in Southern Maryland.
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.
Cheers to Comedy on Friday, Aug. 28 (7-9:30 p.m.), at Running Hare Vineyard, Adelina Road, Prince Frederick – Enjoy a night of laughs during this 21-and-older comedy show featuring adult material and language. Doors open at 7 p.m., and the show begins at 8 p.m. Ticket required.
Lunar Eclipse Paint Night: Light, Release & Renewal on Friday, Aug. 28 (6 p.m.), at WhataBoba, 232 Town Square Drive, Lusby, MD – A guided paint night themed around release and renewal under the lunar eclipse. Ticket required.
159th Annual Jousting Tournament and Bazaar on Saturday, Aug. 29 (10 a.m.), at Christ Church, 3100 Broomes Island Road, Port Republic, MD – One of the region’s longest-running traditions returns as riders compete in Maryland’s official state sport, with a bazaar of vendors and food on the church grounds. Free admission.
Beachside Yoga Flow at The Cottages at Plum Point on Saturday, Aug. 29 (9 a.m.-noon), at The Cottages at Plum Point, 5130 S. Cabin Drive, Huntingtown – Enjoy a 60-minute gentle yoga flow followed by light refreshments, a charcuterie box and time to relax on the beach. Bring a beach chair or blanket. Tickets required.
Back To School Free Event — Love Your Neighborhood Block Party on Saturday, Aug. 29 (1-3 p.m.), at All Aboard Child Development Center, 270 Bugeye Square, Prince Frederick – Families can enjoy games, activities, lemonade, snacks, giveaways, prizes and community resources during this free neighborhood celebration. Register for free to attend.
On Pins and Needles on Saturday, Aug. 29 (2–4 p.m.), at Calvert Library Southern Branch, Prince Frederick, MD – Fiber crafters of all skill levels gather to knit, crochet or embroider together; bring your own yarn. Registration requested. Free admission.
Mully’s Music Bingo: Drinking Songs on Saturday, Aug. 29 (4–6 p.m.), at Mully’s Brewery, 141 Schooner Lane, Prince Frederick, MD – A drinking-songs-themed round of music bingo at the Prince Frederick brewery. Free admission.
Movies on the Beach: Lilo & Stitch on Saturday, Aug. 29 (dusk), at the Waterfront, 9023 Bay Avenue, North Beach, MD – A free outdoor movie projected on a large inflatable screen on the sand; bring a chair or blanket. Free admission.
Campfire & Hayrides on Saturday, Aug. 29 (8–10 p.m.), at NRC Solomons, 13855 Solomons Island Road, Solomons, MD – A summer tradition at the campfire pit between the log cabins and group campsites, with s’mores kits for the first 75 guests, a hayride and songs around the fire. Open to all with base access. Free admission.
Outdoor Movie Night: Hoppers! on Saturday, Aug. 29 (8 p.m.), at Kellam’s Field Complex, 3825 Gordon Stinnett Ave., Chesapeake Beach, MD – A family-friendly movie under the stars on the town’s large outdoor screen; bring blankets or lawn chairs. Free admission.
Tea & True Tales: Guernsey Literary and Potato Peel Pie Soc. – Afternoon Book Club on Tuesday, Sept. 1 (2–3 p.m.), at Calvert Library Southern Branch, Meeting Room – Adults and seniors are invited for tea, treats and a discussion of “The Guernsey Literary and Potato Peel Pie Society” by Mary Ann Shaffer and Annie Barrows. Registration required. Free admission.
Family Roller Skate every Sunday (2 pm to 5 pm), located at Leonard Hall Recreation Center, 23150 Leonard Hall Drive, Leonardtown, MD – The indoor arena provides the perfect space for users of all abilities to join in the fun with music and fun! Entrance fee can be paid in advance online.
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.
Cows, Cars & Classics on Friday, Aug. 28 (5 p.m.), at Chick-fil-A La Plata, 107 Drury Drive, La Plata, MD – A relaxed evening for car enthusiasts and families, with classic and custom cars on display, Chick-fil-A favorites, menu-item samples and a free small beverage for participants. Free admission.
Summer Friday Special on Friday, Aug. 28 (noon–5 p.m.), at Southern Maryland Paintball, 11272 Edge Hill Road, Newburg, MD – The last Summer Friday special of the season, including rental marker, rental mask, 400 paintballs and all-day play. Tickets required.
Mystical Monarchs: Our Amazing Migratory Butterflies on Saturday, Aug. 29 (9–9:45 a.m.), at Wild Birds Unlimited, 58 Shining Willow Way, La Plata, MD – Education Director Mike Callahan presents on Monarch tagging and their fall migration, with a possible live tagging and release demonstration. Advance reservations required. Free admission.
Shops at Waldorf Center Classic Car Show on Saturday, Aug. 29 (9 a.m.–3 p.m.; rain date Sept. 5), at Shops at Waldorf Center, 3018 Festival Way, Waldorf, MD – DMV Rod’s & Classic’s Car Club hosts a car show open to all makes and models, with 139 trophies awarded, food vendors, live music and raffles. Car registration is onsite the day of the show. Free admission.
Hot Rod Saturday on Saturday, Aug. 29 (11 a.m.–2 p.m.; rain date Sept. 12), at All American Harley-Davidson, 8126 Old Leonardtown Road, Hughesville, MD – A relaxed classic car, hot rod and muscle car meetup with barbecue from CrackShack BBQ — no judging, just good rides and good company. Free admission.
Wood and Canvas Family Workshop on Saturday, Aug. 29 (11 a.m.–2 p.m.), at AR Workshop La Plata, 317 Charles Street, La Plata, MD – A guided family DIY session creating a custom wood-and-canvas home decor piece with paints and non-toxic stains. Tickets required.
Freedom Bash on Saturday, Aug. 29 (11:30 a.m.–4 p.m.), at Hughesville Volunteer Fire Department, 15245 Prince Frederick Road, Hughesville – Hosted by the NWTF Southern Maryland Chapter, the event features drawings every 10 minutes, raffles, a silent auction and additional gun raffles. Soda, beer and wine are included with tickets. Ticket required.
1st Annual “Pick Your Own Grapes” Event on Saturday, Aug. 29 (noon–4 p.m.), at Amber View Vineyard, 14600 Banks Odee Road, Newburg, MD – Stroll the vineyard and pick fresh Chambourcin grapes straight from the vines, with hot dogs, chips and outdoor picnic space available; guests may bring their own wine. Free admission; grapes $1.50/lb.
Cute and Courteous Canines on Thursday, Sept. 3 (10:45–11:45 a.m.), at Charles County Public Library, La Plata Branch, 2 Garrett Avenue, La Plata, MD – Meet and interact with certified therapy dogs, courtesy of Southern Maryland Pets on Wheels. Free admission.
DCVYBE @ Piano Keys Lounge on Thursday, Sept. 3 (6 p.m.–11:45 p.m.), at Piano Keys Restaurant & Lounge, 7651 Matapeake Business Drive, Brandywine, MD – A weekly Thursday night of entertainment and live music. Free limited admission before 7 p.m.
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. 28–Sept. 3, at Toot’s Bar, 23971 Mervell Dean Road, Hollywood, MD – Enjoy a full week of live music and entertainment featuring Buff Husky, Social, Moonshine Vagabond, Dance Hall Ghosts, Barstool Bingo, Corn Hole Fun League, Tiff’s Karaoke, Queen of Hearts and Beer Pong.
FNM!!! Friday Night Magic on Friday, Aug. 28 (6–10 p.m.), at Swords and Spoons, 22599 MacArthur Blvd. Suite 126, California, MD – A weekly Magic: The Gathering night open to veterans and newer players, playing commander with occasional drafts. Ticket required.
Under the Night Stars in Puerto Rico Latin Dance Night on Friday, Aug. 28 (7–10 p.m.), at El Coqui Restaurant, 21030 Point Lookout Road, Callaway, MD – A bachata lesson followed by Latin social dancing with DJ Spinnit, plus Puerto Rican food and drinks. Free admission.
Community Art Event: Paint Native Birds for Re: Bloom on Saturday, Aug. 29 (noon–4 p.m.), at Lexington Manor Passive Park, 21675 South Coral Drive, Lexington Park, MD – Residents of all ages are invited to help create the next installment of Re:Bloom, a yearlong public art project bringing more than 100 colorful, hand-dyed tapestries of native plants and wildlife to Lexington Manor Passive Park. Free admission.
Leonardtown Crab Walk on Saturday, Aug. 29 (noon–11:30 p.m.), at Leonardtown Square, 22695 Washington St., Leonardtown, MD – A self-guided crawl through 15 downtown businesses offering crab-inspired bites, specialty drinks and local shopping. Free admission.
U-Cut Flower Experience on Saturday, Aug. 29 (noon–5 p.m.), at Dixon Family Farm, 27075 S. Sandgates Road, Mechanicsville, MD – Cut your own flowers straight from the fields, with cups and clippers provided and a farm shop selling lavender goods and gifts; shaded picnic tables available, no pets permitted. Free admission, flower prices vary.
Changing Landscapes Tour on Saturday, Aug. 29 (1–2 p.m.), at Historic St. Mary’s City, 47414 Old State House Road, St. Mary’s City, MD – A guided walking tour of recent archaeological discoveries at St. Mary’s Fort, spanning 8,000 years of Native presence. Rough terrain; registration required at the Visitors Center. Ticket required.
Jazz and Wine Music Series on Saturday, Aug. 29 (6–8 p.m.), at Corteau Vineyards, 38713 Golden Beach Road, Mechanicsville, MD – Live jazz paired with award-winning wines in a vineyard setting, with admission including a complimentary glass of wine or sangria. Ticket required.
SOMD Cars & Coffee on Sunday, Aug. 30 (8–11 a.m.), at Laurel Glen Shopping Center, 46315 Alton Lane, California, MD – Southern Maryland’s car community meets up to show off rides — no burnouts, revving or reckless driving. Free admission.
Pokémon World Championship Celebration on Sunday, Aug. 30 (8 a.m.), at Swords and Spoons, 22599 MacArthur Blvd., Suite 126, California – Watch the 2026 Pokémon World Championships finals live from San Francisco while trading cards, battling with other players and connecting with fellow Pokémon fans. Attendees are encouraged to bring a deck and wear their favorite Pokémon gear.
Free Military, Veteran & First Responder Kayak Paddle on Thursday, Sept. 3 (5:30–7:30 p.m.), at Greenwell State Park, 25410 Rosedale Manor Lane, Hollywood, MD – A guided two-hour sunset paddle on the Patuxent River, free for military, veterans and first responders. Advance registration required. Free for eligible participants.
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 28th
3:00pm – Bubba Strange – Call Signs – Lexington Park MD
4:00pm – Girl Crush – Nationals Park – Washington DC
5:00pm – Carla Simpson – Mully’s Brewery – Prince Frederick MD
5:30pm – Monkey Business – Running Hare Winery – Prince Frederick MD
5:30pm – No Go Romeo – Fager’s Island – Ocean City MD
6:00pm – Jason Bishop – Happy Harbor Restaurant – Deale MD
6:00pm – Billy Breslin – Ruddy Duck Brewery & Grill – Solomons MD
6:00pm – California Bob – Stoney’s Clarkes Landing – Hollywood MD
6:00pm – Bumpin’ Uglies / Wesley Spangler – The TIKI Bar – Solomons MD
6:00pm – Backstage Pass – Wheel House Beer Garden – North Beach MD
6:00pm – Never 2 Late – Seabreeze Tiki Bar – Mechanicsville MD
6:00pm – Chris Dean – Southern Trail Distillery – Mechanicsville MD
6:00pm – Doc Lohn – Dockside Restaurant & Sports Bar – Deale MD
6:30pm – Shaun Gomban – Blue Fish Pub – Solomons MD
7:00pm – Pete Best – Pirates Cove Dock Bar – Galesville MD
7:00pm – Jeff Durahm – The Potomac Gardens – Colton’s Point MD
7:00pm – Mariah Jean Music – The Scuttlebutt – Cobb Island MD
7:00pm – Hometown Band & Horns – Swan Point Country Club – Issue MD
7:00pm – Dueling Pianos – Town Hall Concert Series – La Plata MD
7:00pm – Jim & Carl – Round Midnight Duo – Bugeye Grill – Solomons MD
8:00pm – Jack Allen – Olde Town Pub – Leonardtown MD
8:00pm – Buff Husky – Toots Bar – Hollywood MD
8:30pm – Myles Deep Band – Annapolis Smokehouse – Annapolis MD
Saturday – August 29th
12:00pm – Myles Deep Duo – Wharf 38 – Deale MD
12:30pm – Greg Floberg – Running Hare Winery – Prince Frederick MD
1:00pm – Shane Graham – Xella Winery & Vineyard – Mechanicsville MD
2:00pm – Mariah Jean Music – Port of Leonardtown Winery – Leonardtown MD
2:00pm – Alan Prather – Corteau Vineyards – Mechanicsville MD
2:00pm – Nightcap – Robin Hill Farm & Vineyard – Brandywine MD
2:00pm – Hyland Brothers – Ketch 22 Restaurant – North Beach MD
3:00pm – Midnight Sunsets – The Boathouse @ Anchored Inn – Deale MD
3:00pm – Kevin Lee – Skipper’s Pier – Deale MD
3:00pm – Southbound 4 – The TIKI Bar – Solomons MD
3:00pm – Levi Stephens – Pirates Cove Dock Bar – Galesville MD
5:00pm – Ryan Moran – Happy Harbor Restaurant – Deale MD
5:30pm – Sister Midnight – Running Hare Winery – Prince Frederick MD
6:00pm – Kevin Howard Jazz – Corteau Vineyards – Mechanicsville MD
6:00pm – Monkey Business – The Pier House – Newburg MD
6:00pm – Hate The Toy – Seabreeze Tiki Bar – Mechanicsville MD
6:00pm – Michael Ferro – Stoney’s Clarkes Landing – Hollywood MD
6:00pm – Vicki Roberts Band – Dockside Restaurant & Bar – Deale MD
6:00pm – Unfinished Business – Breten Bay Golf Club – Leonardtown MD
6:00pm – Swamp Weasels – Blue Fish Pub – Solomons MD
6:00pm – Myles Deep Band – Wheel House Beer Garden – North Beach MD
6:30pm – Funkzilla Unplugged – Bugeye Grill – Solomons MD
7:00pm – Lost & Found – Pirates Cove Dock Bar – Galesville MD
7:00pm – Joey Tippett & Highway Ramblers – Back Road Inn – Leonardtown MD
7:00pm – Shaun Gomban – The Brass Tap – California MD
7:00pm – Justin Jeansonne – The Potomac Gardens – Coltons Point MD
7:00pm – Joe Cox Band / Trace Haggard – The Rex Theatre – Leonardtown MD
7:30pm – Amish Outlaws – The TIKI Bar – Solomons MD
8:00pm – Mike Trujillo – ABC Liquors & Lounge – California MD
8:00pm – Three of a Kind – Buckets Bar & Grill – Lusby MD
7:00pm – Dillon Bodiford – Olde Town Pub – Leonardtown MD
8:00pm – Social – Toots Bar – Hollywood MD
8:00pm – HydraFX – The Taphouse 1637 – California MD
Sunday – August 30th
2:00pm – Justin Allen – Port of Leonardtown Winery – Leonardtown MD
2:00pm – Pete Best – Wharf 38 – Deale MD
2:00pm – Shaun Gomban – Fitzies Restaurant & Pub – Leonardtown MD
2:00pm – Anthony Broccolina – Pirates Cove Dock Bar – Galesville MD
2:00pm – Loveboat Yacht Rock – Rod ‘N’ Reel Resort – Ches.Beach MD
2:00pm – John Luskey – Seabreeze Tiki Bar – Mechanicsville MD
2:00pm – Greg Barrick – Skipper’s Pier – Deale MD
3:00pm – Doc Lohn – The Scuttlebutt – Cobb Island MD
3:00pm – Monkey Business – Stoney’s Clarkes Landing – Hollywood MD
3:00pm – Faron Hamblin – The Pier House – Newburg MD
3:00pm – Hyland Brothers – Dockside Restaurant & Sports Bar – Deale MD
3:00pm – Moonshine Vagabond – Toots Bar – Hollywood MD
3:00pm – David Hamner & Chris Dean – Apehangers Bar – Bel Alton MD
4:00pm – Ryan Keith – Happy Harbor Restaurant – Deale MD
4:00pm – Shane Graham & Julia Baddour – Running Hare – Pr. Frederick MD
5:30pm – Billy Breslin – Bugeye Grill – Solomons MD
6:00pm – Kurt Gibbons – Pirates Cove Dock Bar – Galesville MD
Monday – August 31st
2:00pm – Dance Hall Ghosts – Toots Bar – Hollywood MD
Tuesday – September 1st
6:30pm – Mike Mead – The Tavern – Saint Leonard MD
7:00pm – Open Mic w/Derek Norris – Twisted Bar & Grill – Hollywood MD
Wednesday – September 2nd
5:00pm – Mike Hauer – Ketch 22 Restaurant – North Beach MD
7:00pm – Open Mic w/Steve Nelson – The Tavern – Saint Leonard MD
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