Castine offers travelers several ways to explore: coastal trails with views of Penobscot Bay, the military history of Fort George, historic buildings, and sea kayaking. When planning your visit, you can focus on nature, local history, or experiences on the water.
Coastal Trails, Woods, and Winter Activities
In Witherle Woods, more than 4.3 miles of trails wind through a scenic coastal landscape rich in military history. The trails offer views of Penobscot Bay. In winter, volunteers groom the cross-country ski trails; if you’re planning winter activities, it’s worth checking the latest grooming conditions.
The 100-acre Rene Henderson Preserve includes mixed-forest uplands and diverse wetlands. Its 1.7-mile network of woodland roads and trails offers opportunities to observe birds and other wildlife. In winter, you can skate on the pond once it has frozen over safely.
The two preserves offer different experiences: Witherle Woods combines trails through a coastal landscape with military history, while the Rene Henderson Preserve brings together woodland and wetlands with opportunities for wildlife watching. This can help you choose nature experiences based on the landscapes that interest you most. Cross-country skiing and ice skating are additional seasonal options, although skating depends specifically on the ice being safe.
Fort George and Castine’s History
Fort George was the last British fortification to be evacuated after the American Revolutionary War. The site consists of square earthworks approximately 200 feet long and ten feet high. Fort George offers a tangible connection to Castine’s military history, while the recorded measurements also give you an idea of the earthworks’ shape.
The Castine Historical Society is based at the Town Common in two historic buildings: the 1859 Abbott School Building and the 1850 Grindle House. Its permanent and changing exhibitions, lectures, walking tours, and historical reenactments explore the people, events, and places that shaped Castine and the surrounding Bagaduce River region. Tours of the Perkins House offer a glimpse of life in Castine in the late 18th and early 19th centuries; tour dates are seasonal.
The Historical Society’s 2026 program included free, one-hour walking tours on Fridays, Saturdays, and Mondays from June 20 through October 12. If you’re visiting later, check the schedule in effect at that time.
Sea Kayaking in Penobscot Bay
Castine Kayak Adventures is based on the Castine waterfront and offers guided sea kayaking tours and introductory classes in Penobscot Bay. Small-group eco-tours offer opportunities to observe coastal wildlife and birds and learn more about marine ecology, geology, and local maritime history. The program also includes evening paddles, including tours featuring bioluminescence and stargazing.
The offerings vary by time of day and focus: introductory classes and guided sea kayaking tours are available alongside eco-tours and special evening trips. If you’re planning one of these activities, check the provider’s current schedule in advance, as its offerings may change.
Practical Information for Planning Time on the Water
The floating docks at Town Dock are available from May 15 to October 15. Docking is limited to two hours between 9:00 a.m. and 5:00 p.m.; berths are available on a first-come, first-served basis. If you’re factoring Town Dock into your plans, check the information before you arrive.
Explore more destinations: Southwest Harbor, Surry, Bar Harbor, Mount Desert, East Holden, Orland, Gouldsboro, Ellsworth
For the broader travel overview: Hancock.
