Fly to Boston
Fly from New Orleans to Boston, transfer to your downtown hotel, and settle in. Welcome dinner with your tour director.
If you only see New England in autumn once, this is the trip. We start in Boston, walk the Freedom Trail, then move west into the Berkshires and up through Vermont — the syrup farms, the covered bridges, the Trapp Family Lodge of Sound of Music fame. Up to New Hampshire for the Mount Washington Cog Railway and a cruise on Lake Winnipesaukee. Down through Maine for the lobster dinner you came for. Eight days, seven hotel nights, fly-and-coach format so you don't lose two days driving up and back.
Tour Highlights
- Boston's Freedom Trail
- The Berkshires of western Massachusetts
- Vermont's maple syrup farms and the Trapp Family Lodge
- Mount Washington Cog Railway in New Hampshire
- Cruise on Lake Winnipesaukee
- Maine lobster dinner on the coast
Day by Day
Boston & the Freedom Trail
A full day in Boston walking the Freedom Trail with a local guide — Faneuil Hall, the Old North Church, Paul Revere's house, the USS Constitution. Free time in the afternoon for the harbor or Beacon Hill.
The Berkshires
Travel west into the Berkshires, the rolling hills of western Massachusetts. The fall color in this region is some of the best in New England. [ITINERARY DETAIL: Add specific Berkshires stop and overnight location from your WeTravel itinerary.]
Vermont: Maple, Mountains & the Trapp Family Lodge
Up into Vermont for a working maple syrup farm, the rolling green-and-gold hills, and a visit to the Trapp Family Lodge — the Stowe estate built by the von Trapp family of Sound of Music fame. The setting is unforgettable.
Mount Washington Cog Railway
Cross into New Hampshire for the Mount Washington Cog Railway — the historic narrow-gauge train that climbs the highest peak in the Northeast. The fall color from the summit is breathtaking, weather permitting.
Lake Winnipesaukee Cruise
A scenic cruise on Lake Winnipesaukee, with the Lakes Region's famous fall reflection on full display. [ITINERARY DETAIL: Add midday stop or museum visit from your WeTravel itinerary.]
Maine Coast & Lobster Dinner
Travel east to the rocky Maine coast for the trip's signature lobster dinner — fresh, simple, and exactly what you came for. Walk the harbor town in the afternoon.
Fly Home
Transfer to the airport and fly home, arriving in New Orleans the same day.
What's Included
Included
- Roundtrip airfare
- 7 nights' hotel accommodations
- 14 included meals
- All admissions on the itinerary
- Motorcoach transportation throughout New England
- Professional tour director
Not Included
- Gratuities for tour director and driver
- Meals not listed
- Personal purchases and souvenirs
- Travel insurance (recommended)
Frequently Asked Questions
Is this trip strenuous?
It's an active trip but not athletic. The Cog Railway is a seated train ride. Walking days in Boston and the harbor towns are at your own pace.
Will we hit peak color?
Early October is generally peak in northern New England, with peak shifting later in the southern Berkshires and Maine coast. The route is built to chase the color south as the trip progresses.
What if it rains?
New England in October often has a mix of weather. Bring a real rain jacket, layers, and waterproof shoes. Most stops have indoor backup options.
Are single rooms available?
Yes — ask about the single supplement.
How big is the group?
Group sizes for our fly-and-coach tours typically run 25–40 travelers.