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 visiting Boston, we took the opportunity for a short leaf peeping road trip in New England, before looping back to Boston to fly home. Thinking of making a similar trip? Here are some ideas for planning your trip.
Why Boston, Massachusetts?
The question should be why not go to Boston, Massachusetts?
Boston has a bit of everything, so we discovered – history, water-based views and activities, great opportunities to watch live sports games, cool shopping areas and lots of art and culture. All this, and packaged together in a very walkable and liveable city. Nothing too sparkly or demanding. Comfortable.
In our case, Boston was suggested as the location for birthday celebrations because my friend’s husband likes the singer Ray LaMontagne, and he was playing a gig there in September. We therefore bought tickets to the concert, booked our flights and accommodation, and started to plan our itinerary. Then Ray ‘rescheduled’ his concert to the following year, so we never got to see him after all, but the trip to Boston continued…
A trip of two halves
We spent 3 days exploring Boston with our friends, before parting company to spend 4.5 days on a short leaf peeping road trip to try see some autumnal colours in other New England states.
Itinerary Part 1 – Boston, City Break
Our itinerary for Boston was worked out in consultation with our friends, for obvious reasons. For a good introduction to this fabulous city we planned the following activities:
- Day 1 – Walking the Freedom Trail, eating cannoli in North End and strolling Boston Harborwalk before dinner.
- Day 2 – Walking through the Back Bay Fens to the Isabella Stewart Gardner Museum, before shopping on Newbury Street and then watching the Red Sox at Fenway Park.
- Day 3 – Catching the train to Salem for some Witch tourism.
Itinerary Part 2 – Leaf Peeping Road trip
The itinerary for our leaf peeping road trip was largely determined by the short time we had available. In addition, we were given some great recommendations from a friend who had spent her Honeymoon in New England – bonus!
The benefit of organising a leaf peeping road trip in the New England states is that the states are relatively close together so you can keep the driving distances down. This is where we decided to stop and stay on our short leaf peeping road trip:
- Day 1 – Boston (Massachusetts) to Scarborough (Maine) – 173 km / 108 miles
- Cape Neddick Lighthouse at York, walking the Marginal Way from Ogunquit to Perkins Cove, and exploring Kennebunkport and Walker’s Point.
- Day 2 – Scarborough (Maine) to North Conway (New Hampshire) – 96 km / 60 miles
- Portland Head Light at Cape Elizabeth Lighthouse and Falmouth in Maine, before entering New Hampshire and enjoying the North Conway Scenic Railway.
- Day 3 – North Conway (New Hampshire) to Stowe (Vermont) – 183 km / 114 miles
- Driving the exhilarating Mount Washington Auto Road, checking out the covered bridge in Lancaster and then driving through the trees to Montpelier and Stowe in Vermont
- Day 4 – Stowe (Vermont) to Concord/Bow (Massachusetts) – 215 km / 134 miles
- Exploring Stowe Village, drinking Apple Cider Slushies at Cold Hallow Cider Mill, visiting the Ben and Jerry’s Flavor Graveyard in Waterbury, and driving through Mad River Valley, Vermont back towards Massachusetts.
- Day 5 – Concord/Bow to Boston Logan International Airport (Massachusetts) – 106 km / 66 miles
- Continuing our American History learning journey on Lexington Green and then in Concord, Massachusetts. Also visiting Louisa May Alcott’s home in Concord where she wrote Little Women.
It felt good to finish our leaf peeping road trip in Lexington and Concord, as this brought the trip full circle. We had started our trip with American Revolution history on the Freedom Trail in Boston, which ended with British Redcoats marching to Lexington and Concord, so we were then able to pick the next stage of the history timeline there.
Extending your stay – we saw only a fraction of what’s on offer in this region and the opportunities to extend your trip are endless. With more time, we would have gone further north in Maine and up to Arcadia National Park.
A alternative trip idea is to fly to JFK and drive across Long Island, New York, before taking a ferry across to Connecticut and entering the New England states that way. Check out my Long Island Loop blog for route trip ideas.
Planning practicalities
Online Fall Foliage Updates
As nature is unpredictable then it’s a good idea to check on-line for the fall foliage updates and predictions. We used the Fall Foliage Report on the New Hampshire website, and also the Weather Wise App.
Sadly, despite the best research, the fall foliage colours weren’t the best in the season we visited, which everyone seemed to have a different theory about – the summer had been too dry, it was still too warm. Although not the walls of red and orange I was expecting (is this an unrealistic expectation from Instagram photos with filters I wonder?), the variety of colours in the foliage was still extremely pretty, ranging from greens, golds, oranges to pockets of red.
Flights to the USA
Travel via Dublin from the UK – we caught an Aer Lingus flight from Manchester to Dublin, so that we could clear US customs in Dublin before continuing our journey to Boston Logan International Airport from there. The advantage of doing this is that you save time when you arrive and can be quicker out of the airport, and on to fun things.
Car hire and driving
We booked a car through the AVIS Preferred service, and everything was ready for us when we arrived. So far, we have only had a good experience using this service (so far!). Note – the longest part of the experience was catching the bus from the airport to the car rental area.
To save time on our final day, we decided to collect our rental car on arrival in Boston although we then didn’t use it during our time in Boston. We paid for it to be parked until we were ready to leave – not the most cost-effective option, but it allowed us to leave quickly on the morning of our leaf peeping road trip.
What were the roads like?
The roads were excellent throughout the trip. We left Boston on the Interstate I-95 north after rush hour around 9.30am and it was plain sailing to Maine with no traffic jams.
Once we were off the I-95, we followed a succession of leaf lined roads along the coast and between towns. As we left Maine and entered New Hampshire and Vermont, the roads were a riot of colour from the fall foliage which made for beautiful drives.
Coming back into Boston from Mad River Valley, Vermont, we were back on busier roads but nothing too onerous.
Accommodation options for the road trip
We used Booking.com to source a variety of accommodation on the road trip including: a guest house by a surf beach, a modern Hilton Garden Inn, wonderful ski lodge in Stowe, and functional Hampton Inn hotel in Concord/Bow. Nothing was too luxurious (with the exception of Spruce Lodge in Stowe) as we were just passing through.
However, we had our first experience of a misfire using Booking.com where the accommodation we booked in Montpelier, bore no resemblance to the photos on the listing, or the reviews others had left. We ended up not staying in the room which smelt strongly of bleach (what were they covering up?), but were fully refunded.
Book early for Fall
As October is key leaf peeping season then book your accommodation and activities as early as possible to make sure that you don’t miss out on your priority bookings.
Final thoughts…..
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 then the countryside we experienced in the other states felt a million miles away from urban life – endless multicoloured trees, mountains and farmland, organic food and markets, clapboard churches, and cosy scenes everywhere.
It did not disappoint at all, it was a delight.
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Enjoy your travels!
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