10-Nights New England in the Fall - Tailormade Journeys

A coastal haven steeped in history, Kennebunkport offers a timeless blend of salt-tinged air, centuries-old architecture and sun-warmed beaches where the Atlantic meets riverside charm.

Head to the waterfront for a whale-watching expedition. The journey begins with a scenic cruise along the coast, with insight into the region’s remarkable marine life. Keep watch for finbacks, humpbacks, minkes, the rare blue whale and the endangered right whale, with opportunities to photograph creatures in their natural habitat.

A scenic flight along the Maine coastline to Bar Harbor affords stunning aerial views of Acadia National Park. From above, Mount Desert Island reveals a patchwork of lakes, woodlands, rugged peaks and glacially carved shorelines — perfect for capturing striking photographs of the park’s diverse ecosystem. Upon arrival at Bar Harbor Airport, a private driver-guide takes you into the heart of Acadia for a customized land excursion, showcasing the park’s natural beauty in peak autumn color.

Take in gorgeous views on a scenic drive through New Hampshire’s White Mountains — celebrated for its natural beauty, cultural heritage and historic character — en route to the picturesque town of Woodstock, Vermont.

A private, full-day tour with a local guide begins in Woodstock, where your stroll through the village green reveals Georgian, Federal and Greek Revival homes, along with the Queen Anne-style Rockefeller Mansion, which houses the largest private collection of Hudson River School paintings. The journey continues along Woodstock’s scenic country roads, particularly picturesque during the fall. After lunch, a visit to Quechee Gorge — Vermont’s deepest glacial gorge — offers stunning views of a landscape shaped 13,000 years ago.

As you journey south to Connecticut, pass through the scenic Berkshires — a region of rolling hills and storied villages where world-class arts institutions thrive amid pastoral landscapes. Stops in charming towns such as North Adams, Lenox, Stockbridge or Great Barrington offer a glimpse into the area’s rich cultural heritage and small-town appeal. After a day of exploration, arrive in tranquil Washington, Connecticut.

Today is yours to partake of your inn’s world-class amenities. Take part in hiking, mixology, birdwatching, fly-fishing or cycling through undulating hills. Experience seasonal events such as the harvest moon bonfire, unwind with wellness classes, detox at The Well or indulge in signature spa treatments.

New York’s Hudson Valley stretches along the river’s winding path, where the Catskill and Adirondack Mountains frame historic towns, vineyards and sweeping orchards.

The day unfolds with a full-day Hudson Valley tour that blends the grandeur of historic estates with the charm of Rhinebeck Village. Start with a visit to Springwood, the Gilded Age home and estate of U.S. President Franklin D. Roosevelt, followed by a tour of the Vanderbilt Mansion. Afterward, head to Rhinebeck for lunch, shopping and a walking tour of the village’s historic streets. This afternoon, consider visiting Storm King in Beacon, home to the largest collection of contemporary outdoor sculptures in the United States.

Unwind amid the luxurious amenities at Wildflower Farms or explore the Hudson Valley at your own pace. On-site experiences include hiking, mixology, a Tuthilltown Distillery tour, watercolor classes and pressed flower pottery. For relaxation, indulge in wellness rituals like a sound bath experience, healing reiki session, wellness classes or spa treatments.