Travelling to New England in the fall was a wishlist trip for me, so when a friend suggested a few days in Boston to help celebrate her husband’s birthday, it was a no brainer. After exploring Boston, we set off on a short leaf peeping road trip through Maine, New Hampshire and Vermont, before looping back to Boston to fly home.
Our New England fall road trip was a 5 day loop from Boston through Southern Maine, North Conway and the Mount Washington Auto Road in New Hampshire, and Stowe in Vermont, finishing with American Revolution history at Lexington and Concord. Peak foliage usually runs from late September to mid October.
The question should really be why not?
Boston has a bit of everything, we discovered: history, water based views and activities, live sports, cool shopping areas and lots of art and culture, all packaged in a very walkable and liveable city. Nothing too sparkly or demanding. Comfortable.
In our case, Boston was suggested for the birthday celebrations because my friend’s husband likes the singer Ray LaMontagne, who was playing a gig there in September. We bought concert tickets, booked flights and accommodation, and started planning. Then Ray rescheduled his concert to the following year, so we never did see him, but the trip continued regardless.
And once you are in Boston in the fall, the leaf peeping is on your doorstep. The New England states sit close together, so you can see three of them changing colour without long days at the wheel.
New England · 8 days
We split the trip into two halves.
Exploring the city with our friends.
A loop from Boston through Maine, New Hampshire and Vermont, returning via Lexington and Concord.
The short driving distances are the joy of a New England fall road trip. No leg on our route was longer than 215 km, which left plenty of daylight for lighthouses, mountain roads and cider mills.
Our Boston itinerary was worked out with our friends, for obvious reasons. For a good introduction to this fabulous city we planned the following.
Walking the Freedom Trail, eating cannoli in North End and strolling the Boston Harborwalk before dinner.
Walking through the Back Bay Fens to the Isabella Stewart Gardner Museum, shopping on Newbury Street, then watching the Red Sox at Fenway Park.
Catching the train to Salem for witch tourism and Haunted Happenings country.
The itinerary for our leaf peeping road trip was largely shaped by the time we had, plus some great recommendations from a friend who spent her honeymoon in New England. Bonus.
Our first leg followed the coast north through the bottom corner of New Hampshire and into Maine. Highlights on this drive through Southern Maine:
Cape Neddick Lighthouse. A classic Maine lighthouse stop at York.
The Marginal Way. A beautiful clifftop walk from Ogunquit to Perkins Cove.
Kennebunkport. A smart coastal town worth an amble.
Portland Head Light. The famous lighthouse at Cape Elizabeth.
Coffee in Falmouth, Maine. A quick refuel before turning inland.
Into leafy New Hampshire. The colours build as the mountains rise.
The Conway Scenic Railroad. Watching the foliage in comfort from a heritage train out of North Conway.
The Mount Washington Auto Road. An exhilarating drive to the highest peak in the northeast. Not for the faint hearted.
The covered bridge in Lancaster. A walk through a lovely 1862 landmark.
Montpelier, Vermont. A stroll around America’s smallest state capital.
Breakfast in Stowe Village. The prettiest start to a day on the whole trip. More in our Vermont and Stowe blog.
Cold Hollow Cider Mill. Apple cider slushies and the famous cider donuts.
Ben and Jerry’s Flavor Graveyard. Pay your respects to retired flavours.
Mad River Valley. One of the most scenic drives in Vermont.
Lexington, Concord and the Minute Man National Historical Park. Continuing the American Revolution story.
Louisa May Alcott’s home. The Little Women house in Concord.
It felt good to finish in Lexington and Concord, bringing the trip full circle. We had started with American Revolution history on the Freedom Trail in Boston, which ends with British Redcoats marching towards Lexington and Concord, so we picked up the next chapter of the story exactly where Boston left off.
Peak foliage in New England usually arrives between late September and mid October, moving from north to south, but nature is unpredictable, so check the forecasts close to your trip. We used the Fall Foliage Report on the official New Hampshire website and the Weather Wise app.
Despite the best research, the colours were not at their peak in the season we visited, and everyone had a different theory: the summer had been too dry, it was still too warm. Although we did not get the walls of red and orange I was expecting (an unrealistic expectation from filtered Instagram photos, perhaps?), the variety was still extremely pretty, ranging from greens and golds to oranges and pockets of red.
October is prime leaf peeping season, so book accommodation and activities as early as possible to avoid missing out.
We flew Aer Lingus from Manchester to Dublin so that we could clear US customs in Dublin before continuing to Boston Logan International Airport. The advantage is that you save time on arrival and are quicker out of the airport and on to the fun things.
We booked through the AVIS Preferred service and everything was ready on arrival. So far we have only had good experiences with it. The longest part was the bus from the airport to the car rental area.
To save time later, we collected the rental car on arrival in Boston even though we did not use it in the city, paying for parking until the road trip began. Not the most cost effective option, but it let us leave quickly on the first morning of the leaf peeping loop.
Excellent throughout. We left Boston on the I-95 north after rush hour, around 9.30am, and it was plain sailing to Maine with no traffic jams. Once off the interstate, we followed a succession of leaf lined roads along the coast and between towns. As we crossed into New Hampshire and Vermont, the roads were a riot of colour, which made for beautiful drives. Coming back into Boston from the Mad River Valley we hit busier roads, but nothing too onerous.
We used Booking.com to source a variety of accommodation – a guest house by a surf beach, a modern Hilton Garden Inn, a wonderful ski lodge in Stowe (Spruce Lodge, the one indulgence), and a functional Hampton Inn in Concord and Bow. Nothing too luxurious, as we were just passing through.
We also had our first Booking.com misfire, in Montpelier, where the room bore no resemblance to the listing photos or reviews and smelt strongly of bleach (what were they covering up?). We did not stay, and were fully refunded.
We saw only a fraction of what this region offers. With more time, we would have continued north in Maine to Acadia National Park.
An alternative idea is to fly into JFK and drive across Long Island before ferrying over to Connecticut and entering New England from the south. Our road trip from Long Island to New England covers that route, from the Hamptons to the Berkshires.
In closing
The leaf peeping road trip was the icing on an already iced cake..
New England really is a beautiful part of the world and magical in the fall. Boston felt like somewhere I could live, and the countryside beyond felt a million miles from urban life: endless multicoloured trees, mountains and farmland, organic food markets, clapboard churches, and cosy scenes everywhere.
It did not disappoint at all. It was a delight.
Join thousands of travelers looking for inspiration from our FREE Planet Travel newsletter!
Your step-by-step framework for stress-free, unforgettable trips — from first idea to final itinerary.
Your step-by-step framework for stress-free, unforgettable trips — from first idea to final itinerary.
Join thousands of travelers looking for inspiration from our FREE Planet Travel newsletter!
