Columbus Day weekend in Maryland is an incredible time of transition from summer to autumn, with fall foliage at its peak. Plenty of towns and communities in Maryland celebrate the coming of fall with festivals, fairs, and fun events like parades and brunches. Take advantage of the three-day weekend by taking an unforgettable Columbus Day getaway at one of many Maryland vacation rentals. Check out the most exciting cities and towns in the state.
Consider a Columbus Day weekend getaway in Baltimore, home of America’s oldest Columbus Day parade. Officials in Little Italy host a brunch and parade honoring Columbus, who was Italian, with floats, marching bands, and a wreath-laying ceremony at the statue of Columbus in the town square. While in Little Italy, make sure you check out the wine festival with plenty of great food. Baltimore also has plenty of cultural activities, eateries, and museums all over the city to enjoy on your weekend getaway. Fleet Week is also this weekend, with plenty of boats and planes on display from the U.S. Navy. You might catch a glimpse of the Blue Angels flying overhead.
2. St. Michaels
Columbus Day weekend is a water lover’s paradise if you love small boats. That’s because the weather is perfect, not too hot and not too chilly, for taking a classic small boat onto the Chesapeake Bay at St. Michaels. Discover the Mid-Atlantic Small Craft Festival less than a mile from your beautiful coastal-style cottage vacation rental. After checking out some wonderful vintage sailboats all day, and maybe even hitching a ride on one to get close to the water, grab some chow at Awful Arthur’s Seafood Company or Eastern Shore Brewing.
3. Darlington/Harve de Grace
Darlington is a quaint little village near the Pennsylvania border that celebrates the apple harvest every year. Taste apple pie, apple butter, and fresh apples, and then test your skills in the cornhole tournament. Think about a vacation rental in nearby Harve de Grace for waterfront views of the Chesapeake Bay and the Susquehanna River for a romantic weekend.
Stay at a vacation rental in California, Solomons or Johnstown to take in historic St. Mary’s County. In Hollywood, explore a plantation built in 1703 while tasting the best regional wines Maryland has to offer at the Riverside Winefest at Sotterley. Walk under huge majestic oak trees as you discover St. Mary’s City, where Lord Calvert’s ships first landed in Maryland back in 1635. Drive over to Solomons Island to see Drum Point Lighthouse, a unique octagonal lighthouse restored to serve as a maritime museum.
Enjoy Oktoberfest on Saturday of Columbus Day weekend in downtown Stevensville, a historic town in between Maryland’s western and eastern sections in the middle of the Chesapeake Bay. Sample bratwurst, beer, and pretzels, and try your hand a cornhole tournament. There’s also root beer for the kids. Explore Terrapin Nature Park and its 3.5 miles of trails that wind through wildflower meadows, wetlands, and tidal ponds. Chances are good that you will find a vacation rental with a waterfront view here.
6. Wye Mills
Unincorporated Wye Mills hosts the Wye Grist Mill, the oldest water-powered mill still in use in the United States. The structure was built in 1682, and mill operators explain how the mechanism works on the first Saturday of every month from May to October. While in Wye Mills, the artisans festival features painting, pottery, jewelry, and photos for sale from local artisans. For a fun day of outdoor activities to see the foliage, take a canoe or rowboat out on Wye Mills Community Lake or hike through Wye Oak State Park.
Brunswick hosts its annual Railroad Days on Columbus Day weekend as locals celebrate the railroad’s history in the city. Listen to live music, feast on great food, take in the local restaurants, and, of course, watch trains go through downtown. Buy tickets to take a train ride at the two-day festival, and look at the huge rail yard adjacent to the Potomac River as one of America’s largest rail yards still in operation. Locals love the aptly named Railyard Steakhouse for some homestyle food. This small town is almost like a land time forgot with its historic buildings and quaint houses.
The cool breezes of fall invite you outdoors at Annapolis, home of the U.S. Naval Academy. Weekends, such as during the Columbus Day observance, are also times to enjoy the Maryland Renaissance Festival, the second-largest such festival in the United States. The state capital boasts historic government buildings to see, including the state house that is more than 300 years old. Paca House and Garden features a gorgeous botanical garden in the middle of the city. If you’re lucky, you may see a happy couple having a wedding on the grounds of the house.
The small town with a funny name has quaint vacation rentals that serve as a home away from home. Revel in Oktoberfest at Hard Bargain Farm, an environmental campus where students learn about crops and farming. The family-friendly event happens on Saturday of Columbus Day weekend, and it features live music, food, crafts, fresh apple cider, and wagon rides that go to the Potomac River. If you’re into history, see nearby Fort Washington. For nature lovers, Piscataway Park is a wetlands area directly across the Potomac River from Mount Vernon, George Washington’s home, that harbors beavers, turtles, and bald eagles.
Celebrate honey with your honey or your family thanks to the Honey Harvest Festival in Cockeysville. Activities for the kids include face painting, puppet shows, and animal encounters. Adults may enjoy hive demonstrations, mead making, and beeswax candle dipping along with homemade crafts, blacksmithing, and wool spinning. Boat lovers get out on Loch Raven Reservoir for fishing, canoeing, and motorboating, or take a hike among the many scenic nature trails surrounding the lake. Your vacation rental headquarters could have majestic views of the water.
Rockville has plenty of history and beautiful, antique buildings to see. On the Saturday of Columbus Day weekend, there’s also the annual Rocktobierfest celebration at the Rockville Town Center. Buy a souvenir mug and fill it up with beer from local breweries (responsibly, of course), while enjoying German food and two stages of live music. Rock Creek Regional Park is a nature lover’s paradise during the fall foliage peak with plentiful nature trails and two lakes. Golf lovers have three courses within reach of a vacation rental, including RedGate Golf Course, Woodmont Country Club, and Needwood Golf Course. All three places offer a fantastic way to get outdoors as the warm days of summer come to a close.
Ready to go? Check out these amazing Maryland vacation rentals on Tripping.com.