We’re working from home until further notice, but remain fully operational with uninterrupted access to all our systems.  So it’s very much business as usual.

Search destinations

Fall in New England

  • Boston, Kennebunkport, Lake Winnipesaukee, Stowe, Woodstock, Stockbridge
Autumn in New England Autumn in New England
$ 6774.7302

Winding country roads, quintessential New England towns and glorious fall colors combine on this enchanting road trip through the beautiful states of Maine, New Hampshire and Vermont.

After taking in the historic sights of Boston and the coastal charms of Kennebunkport in Maine, you’ll make your way into New Hampshire - and where better to admire New England’s famous fall foliage than in the second most forested state in America. Scenic backroad drives, hikes and cruises on Lake Winnipesaukee are all on the menu.

Next comes rural Vermont, with stays in the incredibly pretty towns (and leaf-peeping hotspots) of Stowe and Woodstock. From the Green Mountains of Vermont, you’ll drive south into Massachusetts and the softly rolling Berkshires to stay at the historic Red Lion Inn - one of the oldest continuously operated inns in the country.

16 days from
per person
START PLANNING YOUR HOLIDAY
GET IN TOUCH WITH AN EXPERT

Please complete the form below or give us a call on  02031951543

Sign up to receive news and offers*

By submitting you accept our T&C

Interested in:
Autumn in New England

We create tailormade holidays

Create your bespoke itinerary

Contact an expert
Detailed Itinerary
Open all Close all
Day 1-3 London - Boston
London - Boston

You begin with a flight to Massachusetts’ leafy capital of Boston, checking into your upscale boutique hotel in the historic, gas-lit neighbourhood of Beacon Hill.

Boston is wonderfully compact and easily explored on foot. Highlights include following the iconic Freedom Trail, a 2.5-mile-long red-brick path that will lead you past 16 of the main revolutionary sites – including meeting halls, cemeteries and the church steeple where Paul Revere hung his lanterns to warn of the impending British invasion. Otherwise, you can enjoy a visit to the prestigious Harvard University, drop into world-class museums and immerse yourself in Boston’s thriving culinary scene.

Stay: Three nights at XV Beacon Hotel

Day 4-5 Kennebunkport
Kennebunkport

Getting behind the wheel of your hire car, today you’ll leave Massachusetts behind and follow the rugged New England coast up to Kennebunkport in Maine, soaking up some wonderful scenery en route.

A pleasant coastal town full of cafes and pretty beaches, Kennebunkport has been drawing New England’s affluent holiday-makers (including the Bush family) for generations. Enjoy two nights at the eponymous Kennebunkport Inn, a former tea merchant’s mansion and the ideal base from which to explore the town’s characterful sea captain houses, craft shops, seafood restaurants and long, sandy Goose Rocks Beach. Other attractions include the Seashore Trolley Museum with its impressive display of streetcars.

Stay: Two nights at The Kennebunkport Inn

Day 6-7 Lake Winnipesaukee
Lake Winnipesaukee

Your next drive brings you into New Hampshire, one of the best places to admire New England’s famous fall colours with its vast swathes of forest, quintessential villages and winding country roads. Here you’ll be staying at The Inn at Mill Falls which enjoys a lovely location in the foothills of the White Mountains on the shores of Lake Winnipesaukee, the largest lake in New Hampshire’s aptly named Lakes Region.

You’ll find many scenic hiking trails and backroad drives to enjoy in the surrounding area, as well as boat cruises on the lake’s crystal-clear waters – a great way to admire the beautiful foliage along the rocky shores. Return to your hotel for s’mores around the lakeside fire pit.

Stay: Two nights at Mill Falls, Lake Winnipesaukee

Day 8-9 Stowe
Stowe

An even deeper rural experience awaits you across the Connecticut River in Vermont, whose lushly forested mountains transform into a spectacular tapestry of red, orange and yellow each autumn. Driving along the narrow country lanes (past pretty fields and rambling farmhouses) is a great way to admire the incredible colours.

Arrive in the postcard-perfect alpine village Stowe at the foot of Mount Mansfield. Though famed for its skiing in the winter, the fall months offer excellent hiking, climbing, fishing, horseback riding and mountain biking opportunities. Otherwise, you can tackle the world’s fastest zip line course, wander the art galleries in the historic Stowe village and enjoy a guided tour around the nearby Ben & Jerry’s ice cream factory.

Stay: Two nights at The Lodge at Spruce Peak

Day 10-11 Woodstock
Woodstock

You now drive to another leaf-peeping hotspot, Woodstock. This storybook, quintessential New England village lies at the heart of rural Vermont in the midst of rolling hills, farmers’ markets and glorious fall foliage. Experience the America of old with visits to artisan cheese workshops and classic dairy farms – a wonderful insight into Vermont’s farming traditions.

Stay: Two nights at Woodstock Inn

Day 12-14 Stockbridge
Stockbridge

Continue south and you’ll find yourself back in Massachusetts and the softly rolling Berkshires. Home to some of the prettiest villages in the US, this is an enchanting world of wooden churches with pencil fine spires, old-fashioned country stores and elegant, weatherboarded inns.

Head to Stockbridge and the atmospheric Red Lion Inn which dates its founding all the way back to 1773. Tucked away in the foothills of the Berkshires, the property is surrounded by picturesque forests and hundreds of biking and hiking trails leading to majestic overlooks. Whilst here, you should pay a visit to the celebrated Norman Rockwell Museum – home of the world’s largest collection of original Rockwell art – and the Chesterwood Estate, the former home of Lincoln Memorial sculptor Daniel Chester French.

Stay: Three nights at The Red Lion Inn

Day 15-16 Stockbridge - London

Today you will begin your return journey back to London.

  • What was particularly impressive was the way in which Catherine listened to what we like to do and combined all of this in a destination we would not have considered - a truly terrific effort.

    -
    OL, Caribbean