Discover fall in New England.

Arrival and Welcome Reception: Woodstock, Vermont

Arrive in New England via Burlington or Manchester Airports and make your way via private car service to the charming village of Woodstock, Vermont. Check in at the historic Woodstock Inn and unwind from your travels before meeting your fellow guests. As evening falls, we’ll gather for a welcome reception and a special dinner experience at Kelly Way Gardens, setting the tone for a week of fall color, winding roads, and relaxed New England hospitality.

Green Mountains to the White Mountains: Woodstock to Omni Mount Washington

We depart Woodstock and climb into the Green Mountains before crossing into New Hampshire’s White Mountains. The day’s route follows scenic byways, framed by rolling hills, dense forests, and classic New England towns. By afternoon, we arrive at the Omni Mount Washington Resort, where you can enjoy the sweeping mountain views and dinner on property.

Mount Washington Auto Road and Alpine Views

Today’s loop showcases some of the most dramatic scenery in the region. Leaving the Omni, we head toward the Mount Washington Auto Road, where—weather permitting—you’ll have the chance to experience one of the Northeast’s most iconic ascents. After a leisurely lunch in the area, we trace a different route back through the White Mountains to the resort, with plenty of time to relax and take in the evening ambiance and glow of the mountains.

Track Time and Lakeside Living: Omni to Lake Estate on Winnisquam

We pivot from mountain passes to a day focused on driving dynamics. Departing the Omni, we make our way to a local track for a private road-course experience, where you can explore the capabilities of the Porsche model range in a safe, controlled environment. Following lunch, we continue into New Hampshire’s Lake Region and arrive at the Lake Estate on Winnisquam, where a waterside setting and dinner on property provide a tranquil end to the day.

From the Lakes to the Coast: Lake Estate to Kennebunkport

Leaving the lakes behind, we aim for the Atlantic. Our route takes us through classic New England countryside and into the historic seaport city of Portsmouth before continuing along the coast toward Maine. We arrive at Hidden Pond Resort, a secluded woodland retreat near the shoreline, and gather for dinner at Earth, the property’s acclaimed restaurant.

Coastal Byways and Lighthouses

Today is dedicated to Maine’s rugged coastline. We’ll follow a curated loop of coastal roads, with stops in picturesque harbor towns and at some of the region’s signature lighthouses. There’s time built in for photos, seaside strolls, and relaxed exploration before we return to Hidden Pond Resort. In the evening, we celebrate the week with a finale Maine lobster bake, a fitting farewell to New England.

Departures from Portland, Maine

After breakfast, guests depart at their leisure for Portland International Jetport. Whether you choose a direct transfer or a short final drive, you’ll leave with memories of winding mountain roads, coastal vistas, and the distinct character of New England.

*Tour Itinerary and Optional Activities subject to change without notice. Additional on-site costs may be incurred.