Published: April, 2026
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College Tour: Boston, MA- Hanover, NH- Middlebury & Burlington, VT

— Courtney Leary
  • More about your Oliver Guide:
  • Trip type: Family, City
  • Activity level: moderate
  • Ideal length of trip: 5 days

to & from

Fly in and out of Boston and rent a car. We chose to return our car early once in Boston and Uber between schools.
We chose to drive straight to Hanover upon arriving in Boston (2hrs) and then proceed to Middlebury (1.5 hrs from Hanover,) then to Burlington (about an hour from Middlebury) and then back to Boston (3 hours.from Burlington.)

Where to Stay

Hanover, NH (Dartmouth)- Six South Hotel or Hanover Inn
Middlebury, VT (Middlebury)- Swift House Inn
Burlington, VT (University of Vermont)- Hotel Champlain or Hotel Vermont – We stayed at Hotel Champlain, next time might try Hotel Vermont for something with a little more character. The location and amenities at Hotel Champlain were great for our needs though.
Boston, MA (SO many colleges here, Tufts, Boston University, Boston College, Harvard….)-  We stayed at The Charles Hotel, Harvard Square and found it very convenient and because of the incredible upgrade they gave us when our room was not ready (at 6pm) we will always have a special place in our hearts for The Charles. Also recommended to us were The Eliot, The Whitney and The Four Seasons. And, there are even more recommendations in our Boston Oliver Guide.

Where to Eat and Drink

So our trip was not a culinary adventure, we were aiming to find places that would please everyone, especially a growing 17 year old boy who likes things “simple” with a lot of protein. We did a pretty good job. Jessica’s at the Swift House was a highlight and would make any list.
Hanover, NH– Molly’s and Pine for dinner, Lou’s for breakfast or lunch (closes at 3, expect a line, its “famous”) , Dirt Cowboy Cafe for coffee, The Works for quick lunch or breakfast
Middlebury, VT– Jessica’a at Swift House Inn for incredible dinner and breakfast, Haymaker Bun Company for breakfast, coffee or lunch on the rive.
Burlington. VT– The Farmhouse Tap and Grill for dinner, Chipotle or Jersey Mike’s for lunch (LOL) and of course Ben and Jerry’s for dessert
Boston, MA — The options are endless (see Boston Guide for more) but this trip we ate at Henrietta’s table in our hotel one night which was delicious if a little generic in atmosphere and also Alden and Harlow which was hopping and fun with an interesting menu for dinner. We took advantage of the college food options around Harvard Square for lunch, Sweet Greens, tacos etc.

What to Do

The main goal is to visit colleges so sign up for tours well in advance, track down students you might know to meet with and give you the inside scoop. If time allows, attend a sporting event or a performance of some sort depending on your student’s interests.

In all of the towns we visited there were great trails or paths for running and walking. In Hanover, walk around Occum Pond and then head across the street to Pine Park for stunning trails through the woods. In Burlington there is an awesome path around Lake Champlain and in Boston the paths along the The Charles River are never ending. Middlebury also has its share, though a little harder to find, we found a couple of loops on Strava.

What to Pack

Bring serious layers if you are traveling in the fall or spring. We did this tour in early April and it was snowing in Vermont. Temperatures ranged from 25- 65 while we were there. Winter in this region is very very cold so be prepared!

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