New England road trip from Boston

Trip ideas
Duration (in days): 9

From: Boston

To: Boston



Exc. International flights (per person, based on 2 sharing) 
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Self-drive northeastern USA with our New England road trip that begins in Boston before driving through scenic rural New Hampshire, Vermont and Massachusetts. Spend a few days uncovering Boston’s history whilst following the Freedom trail through some of the most important moments of US history. Next, drive north into the White Mountains where you can hike and bike to your heart’s content. Swim in the mountain lakes of Vermont before tasting the local cheeses and wine, finishing your time in New England by visiting the pretty towns of the Berkshires. This classic New England self-drive showcases this scenic region at its very best.

This itinerary can be tailored to suit your requirements please contact one of our consultants to start planning your dream American road trip.


  • Follow the Freedom Trail through the streets of Boston
  • Hike through the lush forests in the White Mountains
  • Take the cog railway to the summit of Mount Washington
  • Taste Vermont’s local cheeses and fresh maple syrup
  • Wander through antique shops in the Berkshires



Itinerary in brief:

  • 2 nights Boston
  • 2 nights North Conway
  • 2 nights Stowe
  • 2 nights Williamstown


Day 1: Arrive Boston

On arrival in Boston you’ll make your own way into the city and check into your hotel for two nights.

Day 2: Boston

Spend the day exploring Boston – we recommend you start by following the Freedom Trail, a route through the city that will take you around 16 different historical sites, from churches and museums to statues and graveyards. For lunch, why not head to the Union Oyster House to try a delicious bowl of New England clam chowder, served here since 1826! Cross the river to explore Cambridge, which is home to both Harvard University and Massachusetts Institute of Technology. In the evening, spend some time strolling the narrow, gaslit streets of Beacon Hill, before settling into a bar and testing some of Boston’s best beers.

Day 3: Drive to North Conway

This morning you’ll collect your car hire from the city and drive north to North Conway, in the heart of New Hampshire. On arrival, you’ll check into your hotel for two nights. Why not spend the afternoon exploring this small town, before getting out into the countryside tomorrow?

Day 4: White Mountains

With a day to explore the White Mountains you’ll want to get stuck into the outdoor activities on offer here straight away. You could go hiking through the forest before swimming or kayaking through one of many high mountain lakes. Another highlight is summiting Mount Washington, whether you tackle the mountain on foot, or head up on the historic cog railway, delivering tourists to the top of the mountain to enjoy stunning views over New Hampshire. Look out for native moose as you drive through the countryside - they are often seen foraging in the lush foothills of the mountains.

Day 5: Drive to Waterbury

Spend the morning taking a final hike through the mountains before driving on to Waterbury in Vermont where you’ll check into your hotel for two nights.

Day 6: Vermont

Spend today exploring northern Vermont. You could drive up to the lakeside city of Burlington where you can wander through the New England style streets before heading to a beach on Lake Champlain to watch the boats. You could also go fishing or try paddle boarding on one of Vermont’s hundreds of lakes or go cycling through the idyllic countryside. Vermont is also famed for its food and drink – you can visit vineyards, taste artisanal cheeses and learn how traditional maple syrup is made. Waterbury, Vermont is also the home of Ben & Jerry’s ice cream – you can take a tour of the factory and learn how this delicious ice cream is made!

Days 7: Drive to Williamstown

This morning you’ll drive south through the Green Mountains before arriving in Williamstown, nestled in the Berkshires in the northwest corner of Massachusetts.

Day 8: The Berkshires

The Berkshires are a famous retreat for city folks from New York and Boston looking for some nature. Pretty Williamstown comes into its own in fall, when the view of the white church spire amongst the brown, gold and red leaves is an iconic image of New England. Spend some time browsing the antique shops in town before driving through the countryside looking for covered bridges and finishing your time in New England with a world-class meal in one of the Berkshire’s finest restaurants.

Day 9: Depart New England

Your time in New England has come to an end – this morning you’ll drive back to Boston Airport, where you’ll return your car hire in time to catch your onwards flight. If you have any time, why not visit Walden Pond on your approach to Boston, the site of Henry David Thoreau’s famous cabin – a sanctuary in the woods around Concord.



New England is famous for its four distinct seasons – snowy winters, fresh springs, hot summers and crisp autumns. Spring is a lovely time to travel for quieter roads and new blooms while fall is the busiest (and most expensive) time as crowds descend to see the famous gold and red leaves throughout the forests of New England.

This itinerary is purely a suggestion, and can be tailor-made to your requirements, so please contact us with your dates and requests and we’ll put together a bespoke quotation for you.

What's included: 

  • Accommodation
  • Boston Harbour Cruise
  • Car Hire

Not included: 

  • Meals
  • Tours not mentioned above


8 nights in 3* standard accommodation.

Hotels in this category include:

  • The Boxer Boston

  • The White Mountain Hotel & Resort

  • Fairfield Inn & Suites by Marriott

  • Best Western Plus Berkshire Hills Inn & Suites


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