5 Fun Summer Activities in and around Chestertown, MD


With our newly announced Sizzling Summer Savings, July is the perfect time for a Great Oak getaway here in Chestertown, Maryland. Summer is always full of excitement, and Chestertown is no different, hosting a variety of activities from golfing to hiking to swimming. Keep reading for a list of 5 fun summer activities for 2016:

1. Biking/Walking/Running along the Wayne Gilchrest Trail (also called the Chestertown Rail Trail): Connecting Washington College to the business district of Chestertown, this 1.2 mile trail is a beautifully peaceful, paved path that’s perfect for foot traffic and cycling.

2. Touring the Eastern Neck Wildlife Refuge: This 2,285-acre island is home to over 240 bird species (including tundra swans and bald eagles!). And don’t miss the Butterfly Garden along Bayview trail, where hundreds of these winged insects come to visit each summer.

3. Relaxing at Betterton Beach: The five acres of this Eastern Shore beach include a fishing jetty, public pier, boardwalk, glistening water for swimming, and soft sand for relaxing.

4. Sip your way through the Chesapeake Wine Trail: We’re only a 30-minute drive away from a few of the wonderful wineries along this trail, so try out the vintages at Crow Vineyard and Winery, The Vineyards at Dogwood, Salisa Winery, and Clovelly Vineyard.

5. Kicking Back in a Kayak: Chester River Kayak Adventures will take you on an eco-tour of our beautiful Maryland waters. Your half-day tour will last around three hours and will include a couple of landings to check out some secluded beaches.

We look forward to seeing you on your summer getaway here at Great Oak Manor! (Don’t forget to check out our Sizzling Summer Savings.)