Nestled between Washington D.C. and Delaware, the state of Maryland is often underrated when it comes to end-of-summer fun. With the Chesapeake Bay running up through the center and barrier islands dotting the coast, this state boasts plenty of unique attractions. Whether you want to enjoy a festival and parade or go hiking one last time before cold weather sets in, Maryland has it all. As for accommodations, there are an abundance of incredible Maryland vacation rentals to choose from. Here are several of the top getaway destinations to consider.
1. Baltimore
The end of August and beginning of September, including Labor Day weekend, is the big Maryland State Fair in Baltimore. This event encompasses all kinds of family-friendly entertainment from carnival games and amusement park rides, to thoroughbred racing and live concerts. Adults can enjoy the garden and home exhibits, while the kids can view the livestock and tour the farm. Naturally, there are plenty of local food vendors to keep you energized throughout your visit. Next, make your way to the Baltimore Comedy Festival, a free four-day event of comedic acts, showcases, art, and panel discussions. Finish with the Defenders’ Day at North Point, a reenactment of the Battle of Baltimore during the War of 1812. This event is a live-action memorial of that fateful battle complete with historic uniforms, arts and crafts, games for kids, live entertainment, and a Fife and Drum Program.
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2. Annapolis
Annapolis, Maryland’s capital, has its First Sunday Arts Festival and Parade during the Labor Day weekend. Not only are there arts and crafts vendors, but there’s also live music, street performers, and artisan food. After picking up some decor for your home or a great painting, head up to the Maryland Renaissance Festival which takes place in the medieval Revel Grove village. This village boasts tons of buildings, theaters, stages, jousting fields, and taverns. Munch on a turkey leg as you enjoy a Shakespearean play in the Glob Theatre. Head to the King’s Field and cheer for your favorite knight or view the reptile exhibit (the closest you’ll get to a dragon). The kids are sure to love the Wee Ones Play Area, Juggling School, and the Pony Ride pavilion.
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3. Ocean City
Ocean City lies just south of Delaware on one of Maryland’s barrier islands. Maryland Week coincides with Labor Day weekend, a last summer hurrah for the entire family. Scope out the best eateries while walking the Boardwalk. Crabs are at their plumpest during this time, so stop by On the Bay Seafood, OCM Crabs, and Blu Crabhouse for some succulent crustaceans. After allowing yourself to digest, rent some kayaks or paddleboards at Odyysea Watersports or Bayside Boat Rentals and explore either the Isle of Wight Bay, Assawoman Bay, or Atlantic Ocean. If you opt for bayside exploration, paddle to the Isle of Wight Management Area for some time out in nature.
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4. Greenbelt
Greenbelt lies nearly halfway between Washington D.C. and Baltimore. If you have a vacation rental here, you can enjoy a Labor Day festival without bearding the D.C. crowds. This little town goes big with amusement rides, carnival games, sports and recreation, art exhibits, craft activities, plenty of food, and – to top it all off – a Labor Day parade. Follow this up with some time hiking in the Patuxent Research Refuge. The Fire Road Trail leads to the Cash Lake and the fishing area.
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5. Crisfield
Remember those plump crabs that come out during August and September? Well, Crisfield celebrates this with the National Hard Crab Derby and Fair where you can play with your food before eating it. There are crab races, crab cooking, and crab picking. All this crustacean fun is complemented with a parade to begin the festivities and fireworks to bring them to a close, arts and crafts, live music and entertainment, and games. Janes Island State Park is right next door, so finish off your vacation strong with some kayaking through the creeks and waterways of the wetland area.
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6. Deal Island
Deal Island is a sleepy little island on the Chesapeake Bay that comes alive during its annual Skipjack Races and Island Festival, which also happens to fall on Labor Day weekend. Sign up the family for a 5k run, and then watch the parades (there are several throughout the 3-day festival). Cheer for your favorite skipjack – Maryland’s official state boat – during the boat races, and even ride one. There’s also a car show, live music, dancing, food vendors, and arts and crafts.
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7. Big Pool
Big Pool uses the last days of summer to celebrate the great outdoors with its Get Into Nature Weekend. This event takes place in Fort Frederick State Park on the Potomac River. You can kayak down the river, join others in a night hike, and tour the historic fort. Interpretive and educational programs help the kids learn about the local wildlife and history. With picnic areas, playgrounds, and shelters, you can bring a picnic lunch with you and enjoy the park all day long.
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8. Cumberland
While Labor Day is celebrated with parades and through nature throughout the state, Cumberland goes unique with the Western Maryland Street Rod Roundup where car lovers unite. Watch classic cars parade down the street, view them up close, and participate in the festive atmosphere. The Roundup isn’t just about cars, though; there’s a corn roast, scenic cruise, live music, and dancing. Head up to Rocky Gap State Park for a refreshing swim in Lake Habeeb and hike along Evitt’s Mountain Homesite Trail.
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9. McHenry
McHenry lies on the northern tip of Deep Creek Lake. Grab a boat rental at the Deep Creek Marina or Aquatic Center and cruise the cool waters. Drive down to Deep Creek Lake State Park, and hike through the forest. If you hike Meadow Mountain Trail where it intersects with Fire Tower Road, you can climb the Thayerville Lookout Tower and enjoy the view. While there, stop at Fireside Deli for some eats. Then hike Swallow Falls for some natural beauty.
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10. Kensington
Kensington is one of the suburbs of Bethesda where you can enjoy the Kensington Labor Day Parade with the kids. Following is a festival with children’s activities, games, and rides as well as plenty of food. If you don’t mind the 30-minute drive down to Washington D.C., take the famous DC Duck Sightseeing Tours and kayak down the Potomac. Thompson Boat Center will help you get all the equipment you need for a successful boating trip. Or head north from Kensington and watch the famous Gaithersburg Labor Day Parade.
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