5 Eastern Shore Destinations Perfect for a Fall Drive

Nov 5, 2015

Driving along Maryland’s Eastern Shore is a wonderful fall pastime. The leaves are changing, vibrant colors are abundant, and you can rest assured Mother Nature has set the perfect background for your weekend getaway. If you’re looking to experience the Eastern Shore this season, visit these must-see destinations:

1. Chestertown

Located in Kent County, this colonial town situated on the Chester River is a historic gem. Surrounded by breathtaking farmland and estuaries, Chestertown offers a variety of restaurants, shops, and an arts scene that keep visitors coming back year after year. Enjoy self-guided tours, theaters, museums, a weekly farmers market, and seasonal events such as Downrigging Weekend, a historic boat festival held the last weekend of October. The town is also noted for its bed and breakfasts, so be sure to stay here for a few days to make the most of your visit.

2. Easton

Brimming with character, this seaside village in Talbot County is the perfect autumn destination. Easton has been named the eighth Best Small Town in America thanks in large part to its beautiful weather, small-town hospitality, and historic charm. The village is home to a fusion of Victorian and Colonial architecture, and the popular Avalon Theatre showcases performances, stand-up comedy, and concerts throughout the fall as well as the rest of the year. Enjoy community walking tours, antiquing, coffee shops, festivals, golf courses, and a great art and music scene during your visit.

3. Cambridge

One of the Eastern Shore’s premier destinations, Cambridge features a historic downtown and iconic Main Street that’s truly one-of-a-kind. Located in Dorchester County, Cambridge hosts seasonal events, such as the Belgian Beer Festival each November, art galleries, boutiques, outdoor recreation, and several noteworthy attractions, including LaGrange Plantation. It’s an authentic Chesapeake town known for its rich history and hospitable services.

4. St. Michaels

Located in Talbot County, St. Michaels draws countless tourists each year thanks to its marina and boating opportunities. Visitors coming here in the fall, however, might prefer to experience the fresh seafood dining options, relaxing spas, and iconic attractions such as the Chesapeake Bay Maritime Museum. The town also hosts War of 1812 reenactments. Thanks to its retail shops, art galleries, parks and trails, walking tours, and other attractions, USA Today voted St. Michaels

Photo by scott1346 | Licensed under cc 2.0