Last week, I told you don’t rush fall—enjoy the final weeks of summer! Well, Labor Day weekend is almost here, and what better excuse do we need to squeeze in one more Maryland adventure before we start thinking about pumpkins, sweaters and everything fall?
Of course, plenty of Marylanders will be heading to the beach for the long weekend. But you don’t have to drive all the way to Ocean City to find something fun to do. From live music and festivals to art, history and a little Eastern Shore charm, there is plenty happening closer to home.
Here are a few ideas for getting out and enjoying Labor Day weekend around Maryland.
🎭 Anne Arundel County — Step Back in Time at the Maryland Renaissance Festival
If you’ve never experienced the Maryland Renaissance Festival in Crownsville, Labor Day weekend gives you three chances—Saturday, Sunday and Labor Day Monday—to step inside Revel Grove.
Think jousting, costumes, live entertainment, food and an entire village that feels like you’ve stepped back hundreds of years. It’s one of those Maryland traditions that’s fun whether you go all-in and dress the part or simply show up ready to people-watch and enjoy the day.
Tip: This is a popular event and can sell out, so check ticket availability before heading out.
🎶 Pasadena — Pops in the Park
Looking for something a little more laid-back? Pack your chairs and blanket and head to Downs Park in Pasadena for Pops in the Park on Saturday, September 5.
It’s a free outdoor concert and a great excuse to pack a picnic, enjoy some music and spend part of your Labor Day weekend outside along the Chesapeake Bay.
🎨 Annapolis — First Sunday Arts Festival
Downtown Annapolis is always worth a visit, but on Sunday, September 6, you can add the First Sunday Arts Festival to your plans.
Stroll along West Street, browse art and handmade creations, grab something to eat and then spend some time wandering through downtown Annapolis or along City Dock.
That sounds like a pretty good Sunday to me!
🎤 Baltimore — Charm City Live
Want something with a little more energy?
Charm City Live takes over War Memorial Plaza on Saturday, September 5, with live entertainment including Boyz II Men and Case, along with DJs, local performers, food vendors, merchants and a Kids Zone.
And here’s an added bonus: admission is free.
If live music is your thing, this may be one of the biggest Labor Day weekend happenings around Baltimore.
🎬 Howard County — Catch a Movie Under the Stars
Sometimes you don’t need a huge festival. Give me a summer evening, a lawn chair and a movie outside, and I’m happy!
Howard County has a couple of options to kick off Labor Day weekend. Columbia’s Lakefront will feature an outdoor movie Friday evening, and Ellicott City has another outdoor movie Saturday night.
It’s an easy, inexpensive way to enjoy one of those final summer evenings outside.
🏛️ Queen Anne’s County — Spend a Day Exploring Centreville
If you’re in the mood for something quieter, take a ride across the Bay Bridge and explore a little Maryland history.
On Saturday, September 5, Queen Anne’s County’s First Saturday activities include free tours at several Centreville locations, including historic Wright’s Chance and Tucker House, the Queen Anne’s County Centre for the Arts and the Kennard African American Cultural Heritage Center.
It’s a nice opportunity to slow down, walk around and learn a little more about Maryland history while you’re at it.
🛍️ Kent County — First Friday in Historic Chestertown
How about starting the holiday weekend on Friday night?
Historic Chestertown holds its First Friday on September 4 from 5–8 p.m. Downtown shops, galleries and restaurants welcome visitors for an evening of art, shopping, food and strolling through one of Maryland’s beautiful historic towns.
If you’ve never spent time in Chestertown, Labor Day weekend might be the perfect excuse.
⛵ St. Michaels — Make It an Eastern Shore Day
And then there’s St. Michaels.
Honestly, you could make an entire Labor Day weekend out of this one.
The St. Michaels Art League Labor Day Weekend Show and Sale takes place Saturday and Sunday, with more than 300 original paintings displayed along Talbot Street.
On Saturday, the Chesapeake Bay Maritime Museum hosts its annual Charity Boat Auction from 8 a.m.–1 p.m., with the live auction beginning at 11. The museum also has Historic Workboat Experience cruises during the day, and there are evening cruises with live music.
Add the shops, restaurants and waterfront scenery of St. Michaels, and you’ve got yourself a pretty wonderful Eastern Shore day trip.
☀️ One More Summer Weekend — Enjoy It!
Labor Day may be the unofficial end of summer, but I’m sticking with what I said last week:
Don’t rush fall.
Maryland gives us so many wonderful places to explore, and sometimes the best adventures aren’t very far from home. Whether you spend the weekend listening to live music, exploring a historic town, watching a movie under the stars, heading across the Bay Bridge or simply enjoying a picnic at your favorite park, take a little time to enjoy these
last days of summer.
Before long, we’ll be talking about colorful leaves, pumpkin patches and everything fall.
But not quite yet.
Happy Labor Day Weekend, Maryland! 🇺🇸
Event schedules, admission requirements and availability can change. Be sure to check with the event organizer before heading out.
Lynn Nichols, Realtor at KW Flagship
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