Fall Road Trip: New England
A few ideas for where to stop for scenic views and quintessential autumn vibes
New England is uniquely positioned for both spectacular foliage and easy road-tripping, making it one of the best destinations this season. Loosely based on a trip I took in September/October of 2021, I’m sharing some of the best places to stop in the region to get your fall fix.
Tip: Plan your trip for the first week in October. You’ll miss the holiday weekend crowds and likely see near-peak colors in northern Maine, New Hampshire, and Vermont.
Boston
We used Boston solely as a launch pad for our trip, but of course, there are a million things to do here if you have the time.
A tour of Harvard is perfect for this fall itinerary. I swear you’ll feel smarter just walking through the quad.
Salem
I shared an entire destination guide for Salem last week, so I won’t go into too much detail here. But, a few must-dos:
Take a self-guided tour at the Witch House
Book a ghost tour or historic walking tour
Eat at the Ledger Restaurant for dinner
Shop at HausWitch for magical trinkets and the best candles
Portland
I was instantly obsessed with Portland. A small city with walkable areas downtown and near the wharf, plus great food and breweries.
Portland Head Lighthouse
Stop here on your way into Portland from Salem. Stretch your legs on the walking paths and admire the view.
Peak’s Island
Take the ferry over first thing in the morning and rent bikes. It’s just under 4 miles around the island and the best way to see the stunning views and amazing homes.
We rented from Brad’s Bike Rental. Take a left when you get off the ferry and you can’t miss it.
If it’s not too muddy, check out Battery Steele, an abandoned WWII bunker, on the far side of the island.
Where to eat and drink
I should do a separate post on all of the places to eat and drink in Portland, but these were the highlights for us:
The Holy Donut
Bissel Brothers Brewing
Duck Fat
High Roller Lobster Co.
Allagash Brewing
Northern New Hampshire
Kancamagus Highway
This is a must-drive for foliage. Winding through the White Mountains, the highway offers scenic view after scenic view. I think I broke a world record for the number of times I whispered “wow” on this section of the trip.
Warning: Expect big crowds if you drive this on a holiday weekend in October.
Mt. Washington Cog Railway
Mt. Washington is known for the worst weather in the world, and boy did we experience it. Our view was obstructed by what I can only describe as a freezing fog and high winds. But, it was still worth the ticket price.
The railway itself is a cool piece of engineering and the staff make it an interesting ride, regardless. A small lodge at the top has warm food (think ski lodge fare) and even a post office.
If you’re lucky to get clear weather, you might see all the way to the Atlantic.
Littleton
Situated between the White Mountains and the Vermont border, Littleton is a charming town with covered bridges and a historic main street. Speaking of which…
Chutters
Littleton might be best known for Chutters—the world’s longest candy counter. You can find almost any candy imaginable, including local maple varieties.
Stowe
Another stop with impressive views and a quaint Vermont village. Take the gondola to the top of Mt. Mansfield (the highest in Vermont) to enjoy the scenery and have a bite to eat at the Cliff House Restaurant.
If you’d rather drive to your views, check out the road through Smugglers Notch.
While you’re in the area, you need to stop by:
Ben & Jerry’s flavor graveyard
The Alchemist Brewery
von Trapp Brewery and the Trapp Family Lodge (yes, those von Trapps)
And of course…
Cold Hollow Cider Mill
Sample hard cider, grab a cider donut, or shop for fall trinkets. It’s everything you could want from this time of year conveniently in one location.
I just got back from a long weekend in central Vermont, so expect a packing list and more recommendations coming very soon!