New England - Fall Foliage Itinerary

Touring most of New England in the fall is a lot like saying you want to visit every winery in Napa Valley. There are simply too many towns and places to see, but if you want to visit as much as possible over a long weekend and be assured you will see peak foliage along the way, this trip will highlight top spots, notes and destinations as you tour five states in five days.

One added advantage is trying to plan a trip months in advance (when hotels are booking and flights are less expensive) takes a bit of guessing as to when the colors will arrive. However, if you plan a trip to move South to North, East to West, up and down, you are pretty much assured of seeing peak foliage along your travels. This trip includes leaves, waterfalls, covered bridges, shopping and amazing food and wine.

Of course, we encourage you to modify stops, lodging and destinations based upon your own preferences and goals when planning your trip.

Travel Note: Timing is the hardest part of planning a trip to New England. You have to time both the changing colors (trying to find peak foliage) as well as all of the events going on in every single town. Below are a few links which may help to time the fall and what is happening on the dates you are traveling.

DAY 1 – BOSTON, KENNEBUNKPORT

Fly into Boston Logan Airport
Market Square – Newburyport, MA – Shopping
Nubble Lighthouse – York, ME – Photo Op
Marginal Way and Perkins Cove – Ogunquit, ME – Short Walk, Shopping and Photo Op

Eat: Earth at Hidden Pond – Potting Shed – Dinner ($$$) – Try the Gnudi (cheese stuffed Gnocchi) and Kimchee
Stay: Hidden Pond – ($$)

DAY 2 – KENNEBUNKPORT, WINNEPESAUKEE, JACKSON

HB Provisions – Shopping for Wine, Beer, Snacks and more
Dock Square – Shopping and to see the Love Locks on the Bridge
Shore/Ocean Road – Drive to see George H. Bush’s home and St. Ann’s Church
Bailey’s Bubble – Wolfeboro, Lake Winnipesaukee ($) – Moose Tracks
Castle in the Clouds – Overlook of Lake Winnipesaukee
Tamworth Lyceum and Distillery – Drink tasting, visit town ($)

Eat: Mornings in Paris – Breakfast, Coffee ($) – Pistachio Macaroons and Pastries
Eat: Mabel’s Lobster Claw or The Clam Shack – Lunch ($$) – Lobster Rolls
Eat: White Mountain Cider – Dinner ($$) – Crab Cakes, Pork Schnitzel, Warm Cider Donuts & Ice Cream
Stay: The Inn at Thorn Hill – Mt. Washington Suite – ($$)

DAY 3 – KANCAMAGUS, SUGAR HILL, STOWE

Jackson Covered Bridge and Jackson Falls – Photo Op
Kancamagus Highway ($) – Top U.S. Scenic Drive with stops for waterfalls, bridges and overlooks
Robert Frost’s House (The Frost Place) – Sugar Hill ($) – Tour
Inn at Sunset Hill – Scenic View and Photo Op
Maple Grove Farms – Maple Ice Creemes ($)
Smuggler’s Notch Drive – Scenic Drive

Eat: The Inn at Thorn Hill – Breakfast Included
Eat: Miller’s Café – Littleton, NH – Yankee Flip Pot Roast Sandwich ($)
Eat: Edson Hill ($$$)
Stay: Edson Hill – ($$)

DAY 4 – STOWE, WOODSTOCK

Trapp Family Lodge – Tour and Photo Op
Emily’s Covered Bridge – Photo Op
Ben and Jerry’s – Quick Tour or Sight Seeing
Route 100 – Waitsfield, Warren, etc. – See Destinations for more details including small towns, waterfalls, hikes, bridges and more.
Gondola Ride – Killington, VT ($$)
Woodstock – Shopping, Sightseeing
Woodstock Middle Bridge – Photo Op
Red Taftsville Bridge – Photo Op
Quechee Gorge – Scenic Overlook

Eat: Cold Hollow Cider – Breakfast ($) – Warm Apple Cider Donuts and Cider
Eat: The Warren Store – Lunch – Sandwiches, Sides – ($)
Eat: Simon Pearce – Dinner ($$$) – Vermont Cheddar Soup, Horseradish Crusted Cod, Sweet Corn Risotto
Stay: Woodstock Inn – ($$)

DAY 5 – WOODSTOCK, WESTON, FLY HOME

Calvin Coolidge Historic Site – Historic Vermont town
Vermont Country Store – Weston – Shopping, Visit Town
Fly Home – Albany, NY, Manchester, NH or Boston, MA