Top Festivities This Fall in Annapolis

Embrace the arrival of fall with its cooler weather, breathtaking foliage, and maritime experiences. Before the chill of winter sets in, take advantage of the unique seasonal charm that graces the area. The perfect time for a family vacation or solo retreat. Nestled within the heart of Annapolis, Annapolis Waterfront Hotel, Autograph Collection offers spacious accommodations and proximity to the area’s best events for the ideal fall escape.

Watch a Navy Football Game

During this season, college football takes center stage as an essential fall pastime. Go support Annapolis Waterfront Hotel’s neighbor, the Naval Academy, at their home turf, the Navy-Marine Corps Memorial Stadium. Even if football isn’t your usual fanfare, the excitement and spirited energy of these games set an electrifying atmosphere that’s impossible to resist.

Go to the Maryland Rennaissance Festival

The Maryland Renaissance Festival is a 40-year-old cherished tradition in Annapolis. The fall spirit is brought to life on these fairgrounds. More than 200 entertainers take to the various stages to perform plays, comedy acts, and more. Afterward make sure to stop by the food stands to enjoy turkey legs, gyros, and a seafood raw bar. This festive event runs for nine weekends and ends on October 22.

Explore the Trails 

Slip away from the streets of Annapolis and head to Lake Waterford Park to reconnect with the great outdoors. This serene park boasts a sprawling 12-acre lake which invites you to partake in shoreline fishing or explore the many hiking trails. As you go on a leisurely stroll around the lake’s perimeter, prepare to be in awe of the vibrant leaf colors; a fall sight that just can’t be missed.

A visit to the Jug Bay Wetlands Sanctuary is an absolute must if you are interested in the local wildlife. This sanctuary is filled with wooden trails that wind over the wetlands, offering an opportunity to witness the fall foliage and diverse ecosystems that call this place home. About 45 minutes away from Annapolis Waterfront Hotel, this is a great day trip option for those wanting to explore more of Maryland.

Celebrate the Annapolis Sail Boat Show

Whether you’re a boat enthusiast or simply want to enjoy a waterfront stroll with family, the Annapolis Sailboat Show is a scenic event everyone can enjoy. During the second weekend of October, City Dock will be lined with an array of sailboats, while exhibitors display the latest in sailing gear and equipment.

Go Leaf Peeping at a Winery

A visit to Great Frogs Winery will make you forget you are still in the city with its stunning landscape. They offer plenty of outdoor seating and room for picnic blankets, paired with an unforgettable vineyard and tasting experience. With a glass of wine in hand, you can simply lean back, allowing the vista to captivate you.

Stop by a Farmers Market

There are many farmers markets scattered throughout the region, but the Anne Arundel County Farmers’ Market is a local favorite. The market takes center stage every Saturday and Sunday during the fall months. With varying market vendors, you can enjoy fresh seasonal varieties and family-friendly events. There’s no better way to get a taste of the area’s local produce, goods, and inviting community spirit.

Experience the Maryland Corn Maze

If you’re seeking a more traditional autumn experience, look no further than the Maryland Corn Maze. With over eight acres to explore in the Gambrills area, the Maryland Corn Maze is a seasonal favorite for all who visit. After traveling through the maze, warm up with apple cider or keep the thrills going with a family-friendly hayride. 

Explore Local Businesses

The fall season in Annapolis wouldn’t be the same without the charm of local businesses throughout the area. For a glimpse of some of Annapolis’ most prized goods, shops, and culinary tastes, head to the historic Main Street. Here, you can head to O’Brien’s Oyster Bar & Seafood Tavern, an Annapolis staple renowned for serving the best crab cake.

When walking through the downtown area, nothing feels better than enjoying the crisp air and local scenery. Annapolis’ very own Forward Brewing provides the perfect setting to enjoy the flavors of finely crafted local brews on a fall evening.

After exploring the area, elevate your stay by enjoying a luxurious visit to Sadona Spa—a wellness favorite at Annapolis Waterfront Hotel. Take time to unwind by priming your body with a peaceful massage or refreshing body treatment.

From the tranquil beauty of autumn walks to the thrill of seasonal festivities, our central location ensures the best of fall in Annapolis. We can’t wait to welcome you to our waterfront haven. At Annapolis Waterfront Hotel, serene views, delicious dining, and communal events make for a fall getaway unlike any other.