NPS / Volunteer Holden Mills
Fall is upon us! Watch as the Chesapeake Bay watershed transforms. Admire the autumn foliage, sip on apple cider at fall festivals, and discover the ghastly lore of historic towns. The watershed offers something for everyone looking for an autumnal adventure.
Below are some great Chesapeake Gateways Network Sites and Experiences and trip itineraries to check out this fall.
Furnace Town Historic Site
Explore Furnace Town Historic Site’s living history village, nature trails, and artisan workshops.
New York Susquehanna Basin Water Trail
The trail highlights the rich natural, cultural, and historical landscapes of upstate New York for paddlers and nature enthusiasts.
Blue Ridge Hills & Hollows
Blue Ridge Hills & Hollows is a bikepacking route that connects people to the history and landscapes of the Blue Ridge Mountains.
Visit St. Mary's County for a day of history and haunting. Infamous for being one of, if not the most, haunting places in Maryland, Point Lookout State Park vaunts history and scenic beauty perfect for a fall day trip. Journey to Historic St. Mary's City and immerse yourself in colonial history. Finally, end your day exploring a chilling story in Leonardtown, MD.
At the meeting of the Potomac and Shenandoah Rivers, this Appalachian town transforms into blushing hillsides. Through October and early November, Harpers Ferry, West Virginia not only boasts scenic overlooks of the river and the golden hills, but many fun fall-filled events that history buffs and ghostly fanatics will love.
In Harpers Ferry, there are a variety of ways to explore. Our itinerary offers some inspiration for everyone, whether you are an avid hiker, casual bike rider, or small-town enthusiast. Make sure to pack a sweater and your hiking shoes!
Enjoy a fall getaway to the Chesapeake region of Virginia, starting in Tappahannock. From Tappahannock, the rest of the region is within easy reach. Just beyond town, wildlife refuges fill with migrating birds and monarch butterflies, while historic homes, state parks, and colonial landmarks tell stories that stretch from the Powhatan communities who first lived along these rivers to the colonists, planters, and watermen who followed. Together, these places offer a closer look at the heritage of the Chesapeake Bay watershed, all wrapped in the golden light of the season. Whether you go for a day, stop for a long weekend, or stay the whole week, it's full of history, scenery, and small-town charm. So, pack your layers, bring your binoculars, and come hungry.
Last updated: November 5, 2026