It's free to join the Travel Community on Pinerary! Join Today
Leaf Peeping in New England

Leaf Peeping in New England

Map of trip
1 Follower
Posted on June 26, 2025

Traveled to see the famed New England in the prettiest time of the year! Leaves, good food, history - this trip had it all.

Trip Recap

  • Day 1: Explored Boston's charming Beacon Hill and enjoyed beautiful parks and delicious food!
  • Day 2: Four states, delicious food, and unforgettable memories in just one day!
  • Day 3: Unexpectedly stunning fall foliage along the Berkshires' Mohawk Trail—truly breathtaking!
  • Day 4: Had a fantastic solo day in Boston exploring and enjoying delicious cannoli!

Highlights

  • Rose Icon

    Foliage on Mohawk Trail

  • Rose Icon

    Lobster Roll in Portland

  • Rose Icon

    Orchard in MA

  • Rose Icon

    Food in Boston

Day 1

Explore Boston!

Today we landed in the afternoon at Logan and headed towards the hotel in Beacon Hill. This is a great place to stay as it's very close walking distance to a lot. We grabbed a quick lunch at Upper Crust Pizzeria right on Charles St in the heart of Beacon Hill and continued to explore. Don't miss the cutest bookstore possibly ever? called Beacon Hill Books & Cafe. Gorgeous!

Then we headed over to Boston Common, a large park right in the middle of downtown Boston. This is also right across the street from the Massachusetts State House. The foliage was gorgeous and the sun was out so it was perfect! We also went through the adjacent Boston Public Garden which was so peaceful.

We went to dinner at The Paramount (also in Beacon Hill) and then headed to the original Cheers bar to cap off the night early before a long day tomorrow.

The Upper Crust Pizzeria
Maybe
No data available
Cheers On Beacon Hill
Must Do
No data available
Boston Common
Must Do
No data available
Boston Public Garden
Must Do
No data available
Beacon Hill Books & Cafe
Must Do
No data available

Day 2

Ok buckle up this is the big one!! 4 States in 1 Day

Got up early for our big adventure day. Picked up a simple breakfast from Flour Bakery + Cafe in Beacon Hill and headed to the Enterprise rental office in downtown.

Once we picked up the car, we headed north 1 hour to Salem, MA. We'd hear so many things about Salem, especially in October, we simply couldn't pass it up. The great foliage on the way was an added bonus! If you are a true Halloween fan, including witches and ghouls and all of that, this is a must. If you aren't (like us), you probably don't neeeeed to stop here. We walked around for about an hour, entering shops here and there, and continuing on with our long journey.

Next, we drove up 2 hours to Portland, ME for a much needed lobster roll. We stopped downtown to get Highroller Lobster Co. It was pretty crowded and there was a bit of a wait, but the fun merch kept us occupied. My friend and I got the mini lobster rolls and they tasted as good as they looked! Tbh I have been thinking about those ever since. We explored Portland afterwards for a bit and then onward to our dinner location in Concord, NH, 2 hours away.

We parked right in front of the New Hampshire State House and walked around it before deciding on Thai for dinner at Siam Orchid Thai Bistro. Kind of random, but ended up being pretty tasty.

Then we drove 2 more hours to West Dover, VT in basically all darkness since the sun was setting so early. I do wish we could've seen this drive during the day as I'm sure it is gorgeous. We stayed on Mount Snow at the Grand Summit Resort and Hotel.

Grand Summit Resort
Must Do
No data available
Flour Bakery + Cafe
Must Do
No data available
The Highroller Lobster Co.
Must Do
No data available

Day 3

Berkshires Mountains

This day was such a surprise. By now, we thought we had seen all the foliage we were going to. But thanks to the awesome concierge at Grand Summit in Vermont, we ended up changing our route to go through the Berkshires in western Mass.

We started with breakfast in town in nearby Wilmington, VT at Dot's Restaurant.

Then we headed towards the Mohawk Trail in the Berkshires. This is where we saw the most beautiful foliage of the trip so highly recommend this for anyone looking for those fall leaves. The Mohawk Trail is basically Highway 2 in Western MA - from North Adams to Greenfield. It took about 2 hours from there back to the greater Boston area, but it was worth every second.

Upon approaching Boston, we actually stopped in Harvard, MA (Not Harvard Univ!) to visit Carlson Orchards, specifically in search of apple cider donuts. Highly recommend adding an orchard to your itinerary for this trip!

We went straight from Harvard, MA to Harvard University in Cambridge, about 1 hour away. We saw Harvard Yard, the big fancy gates, and went in a bookstore or two before heading to our hotel for the night, the Omni in Seaport.

We chose Seaport because it is really close to the airport, and even has a bus that goes straight there. So one we settled in there and returned the car, we headed out again! (I'm exhausted just typing this, I don't know how we did it all!)

This time we hit the Freedom Trail, which any history nerd needs to do, Boston Public Market for some quick food, saw Paul Revere's house, and ended in the North End for Italian food. Quick note: make a reservation for any places in the North End. and bring cash! All the places are great in that area that is known for great Italian!

Mohawk Trail
Must Do
No data available
Freedom Trail
Must Do
No data available
Boston Public Market
Must Do
No data available
North End
Must Do
No data available

Day 4

Explore Boston!

Today my friends ended up leaving pretty early for their flight, so I had a solo day to explore.

I started by walking back to the North End - this was a pretty long walk but it was a gorgeous day so it worked. I went to Mike's Pastry which is very well known for their cannolis! Highly recommend. It is cash only which I found out the hard way until a very very nice Bostonian spot me some cannoli cash.

I spent the majority of my day walking down Newbury Street, lined with trees and shops galore. After a quick lunch nearby, I headed to the last ticket available at the Boston Tea Party museum, located in the middle of the water. It was a great experience and highly recommend, veen if you're solo.

Went back to the hotel and took the bus to the airport and my feet finally got a rest.

Mike's Pastry Boston
Must Do
No data available
Boston Tea Party Ships & Museum
Must Do
No data available
Newbury Street
Must Do
No data available

Anything you would add or do differently?

  • More time! I think if we split up day 2 in to 2 days we would've seen more in the daylight and not been so rushed.