New England Fall Roadtrip: A Guide

Written By Abbie Walker

I love Fall. Like I really love Fall. I do what I can to make the Southern version of the season enjoyable, but it’s always been a dream of mine to make the trip up to New England to see the colorful Fall foliage, breathe in the crisp cool air, and celebrate all things spooky. 

October is hands-down my favorite month, and I knew I wanted to head north then to take advantage of the cooler weather and the Fall vibes. It’s kind of a gamble when the leaves will be at their peak color, but it’s usually best between late September and mid-October. We ended up settling on October 1–8 this year, and it turned out to be so beautiful the more north we went. You can also use this Fall Foliage Map to get a better idea of what the leaves will be like in each area. 

I was so glad my besties Annie, Sherree, and Chelsea were able to join me on this adventure. We definitely crammed a ton of fun into a short period of time—six states in eight days is no joke. But I feel like we got a good idea of each area during our “sampler trip.”

If you’re also wanting to explore New England in the Fall, here’s what I recommend eating, seeing, and doing in each state along the way.


MASSACHUSETTS

Boston

Between the rich history, fresh seafood, and vibrant neighborhoods, there’s so much to do in Boston. You could easily spend a week exploring all that Bean Town has to offer, but here’s some of the places I think you should see.

EAT

  • Abigail’s Tea Room (try five of the original teas thrown overboard during the Boston Tea Party)

  • Joe’s on Newbury

  • Tatte Bakery (several locations around the city)

  • Bell in Hand Tavern (their clam chowder is the best!)

  • Omni Parker House (home of the original Boston cream pie) Pro tip: The hotel gift shop serves the exact same one as they do in the restaurant.

  • North End has an endless supply of authentic Italian restaurants to choose from

  • Mike’s Pastry

  • Cafe Luna in Cambridge

SEE

  • Newbury Street

  • Beacon Hill (Acorn Street is great for pictures)

  • Boston Public Garden and Boston Common

  • Cheers Bar (They didn’t film the show here; it was just the inspiration. So save yourself the claustrophobia inside the bar and just get a picture with the entrance.)

  • Harvard Campus

DO 

  • Browse the shelves at Brattle Bookshop

  • Walk the Freedom Trail

  • Explore the New England Aquarium

Salem

Halloween is my favorite holiday, and I’ve seen Hocus Pocus probably 50 times—so you know I couldn’t pass up the chance to experience Salem during spooky season. Salem’s history is so complex, and there’s a lot to see as a tourist. Overall, it’s a fun city, but it can get pretty chaotic during actual Halloween. So, do what we did and visit earlier in October if you want to have the witchy vibes but avoid the massive crowds and long waits. Also, I recommend taking the train from Boston because there’s not a lot of public parking.

EAT

  • Red Line Cafe

  • Rockafellas

  • Goodnight Fatty Cookies

  • Turner’s Seafood

SEE

  • Old Town Hall

  • Witch House

  • Ropes Mansion

  • Bewitched Statue

  • Max and Dani’s House from Hocus Pocus (4 Ocean Avenue)

  • Oceanfront

  • Pioneer Village

  • Salem Witch Trials Memorial

DO

  • Browse the spooky shops on Essex Street

  • Learn the history of Salem with Witch City Walking Tours (Our guide Rebecca was amazing!)

Concord

When I think of quaint New England towns, Concord, Mass., is definitely on the list. Its literary history and cozy vibes make it the perfect stop for a chill, Fall morning.

DO

  • Grab a pumpkin spice latte from Haute Coffee

  • Step inside the story of Little Women at Louisa May Alcott’s Orchard House (I’ve never felt more like Jo March in my entire life!)

  • Relax at Walden Pond

Deerfield

We didn’t expect to find much as we cut through the west side of the state, but Deerfield had one unique surprise for us—The Yankee Candle Village. Listen, this place was an experience. So many rooms, so many candles. A Christmas village. A medieval castle. Creepy animatronics. I could go on and on, but you really need to see for yourself if you’re ever in West Massachusetts.

PORTLAND, MAINE

Lobster and lighthouses. What else do you need? We loved Portland’s harbor atmosphere and how chill the city was. You can easily do Portland in one day, and I definitely recommend checking it out if you want a taste of Maine but only have time for one city. 

EAT

  • The Holy Donut (their famous potato donuts are delicious)

  • Eventide (amazing lobster rolls!)

  • Portland Lobster Co. (listen to some live music while you crack open ya very own lobsta)

  • Duck Fat

SEE

  • Portland Headlight

  • Bug Lighthouse

DO

  • Browse the shops on Exchange Street

  • Hit up one of the many breweries


NEW HAMPSHIRE

New Hampshire surprised us in the best way. The White Mountains and vibrant Fall foliage were literally breathtaking. If you love to hike or be out in nature, don’t pass up this gorgeous state!

EAT

  • Pub 32 Pizza in Lincoln

  • Schilling Beer Co. in Littleton

SEE

  • Albany Covered Bridge

  • Sabbaday Falls

  • Pollyanna Statue in Littleton

DO

  • Take a drive down the Kancamagus Highway

  • Hike the loop trail to Artist’s Bluff (great sunset view!)

  • Explore Flume Gorge


VERMONT 

Ah, Vermont in the Fall. The cute little towns and cafes. The rolling hills. Hot cider and maple syrup. It’s literally the stuff of Gilmore Girls. If I had to pick one state to go back to—it’s Vermont. Seriously, do yourself a favor and just go. 

EAT

  • Cold Hollow Cider Mill in Waterbury (apple cider, apple cider donuts, apple sandwiches, apple everything)

  • Palmer Lane Maple (maple creemees are the perfect Fall treat)

  • Our House Bistro in Winooski (they have an entire mac n cheese menu)

  • Henry’s Diner in Burlington (pumpkin pancakes, please!)

  • Mon Vert Cafe in Woodstock

SEE

  • Montpelier (Vermont Capital)

  • Von Trapp Family Lodge in Stowe (yes, as in, The Sound of Music Von Trapps)

  • Sleepy Hollow Farm in Woodstock

  • Middle Covered Bridge in Woodstock

DO

  • Take a tour of Ben and Jerry’s factory in Waterbury (be sure to pay your respects at the flavor graveyard)

  • Walk down the streets in Stowe and Woodstock

  • Drive along Smugglers Notch Pass

  • Shop the Church Street Marketplace in Burlington

  • Relax along Lake Champlain’s waterfront park in Burlington


PROVIDENCE, RHODE ISLAND

We stayed in Providence for our last night—mostly just to check Rhode Island off the list. It’s a quirky town, but there’s some cool spots and friendly people.

DO

  • Grab some coffee milk at Dave’s Coffee (it’s the official RI state drink)

  • Explore Brown University’s campus

  • Pop into Frog & Toad (West) for some cute gifts and RI souvenirs

As you can see, we did a lot in a short amount of time. But I feel like we really got to see what New England is all about. Definitely make it a goal to visit these gorgeous states in the Fall. I think if I were to go back, I’d love to do a coastal trip from Connecticut to Maine in the summer because there are so many cool seaport towns to explore.

I hope this guide has inspired you to plan your own New England adventure! 🍁







Abbie Walker