The New England Autumn is world-renowned, and well worth it. A couple weeks ago we decided to check out this famed part of the US during the Fall and I can’t stop raving about it. The colors were incredible, the scenery stunning and the small towns to die for. So if you’re thinking of doing you’re own Fall road trip in the North East of the US, here is the best Autumn weekend road trip from Boston, a great city to base out of in order to see the most of this part of the country. You’ll roam through the college towns of New Hampshire, the rolling hills of Vermont and the scenic byways of Massachusetts on this feast for the eyes journey! And if you only have a weekend to see it, that’s ok! While you could drive this part of the country for weeks seeing all there is to see, here’s the best way to see the most in a weekend!
Day 1 – Leave Boston bright and early!
Drive from Boston to Hanover, New Hampshire, the home of the famous Dartmouth University and lovely little North Eastern town, complete with grassy lawns and falling leaves.
Stop for Lunch at Molly’s Restaurant and Bar for clam chowder and wood fired pizzas in a cozy pub-like atmosphere.
Jump back in the car and head to the outskirts of Woodstock, Vermont – specifically headed toward the Sleepy Hollow Farm in the rolling foliage covered hills of Vermont.
This breathtaking off-the-beaten-path farm is magnificent in the Autumn, with leaves all around and the colors of the rolling hills looking like an oil painting. Stop for a while and take in the scenery here in the backroads of Vermont, an area that will for sure keep your eyes fixed on all the beauty around you!
When you’re ready to head on, drive the 10 minutes down the hills into Woodstock itself, the most beautiful little town you might ever see. Woodstock, Vermont is quite literally out of a story book, with colonial houses lining the main street, blocks from the town butcher and market. Spend some time here just admiring the best of small town USA, amidst the falling leaves and the Autumn colors.
Once you’re done admiring one of the most beautiful places in the US, jump back in the car and drive over the mountains to Manchester, Vermont. Along the way though, be sure to stop at Plymouth Artisan Cheeses along Vermont Route 4. Pick up maple syrup, Vermont cheddar cheese and homemade apple butter!
After your quick stop to pick up Vermont’s finest artisan products, head back out on the road towards Manchester, Vermont where you’ll stay for the night. On the road you’ll climb in elevation, crossing the Green Mountains and take in the gorgeous scenery of the drive.
Once in Manchester, Vermont, make your way to the gorgeous Taconic Hotel, a Kimpton property in this cute little New England town. Here you’ll stay for the night, cozy in the hotel and eating dinner next to a roaring fire at the hotel restaurant, the Copper Grouse.
Day 2 – Sleep in, then get back on the road bound for Massachusetts!
In the morning on Day 2, take your time getting up and around and enjoy the coziness of the Taconic Hotel, especially on chilly Fall days! When ready, head out of Manchester, Vermont towards Williamstown, Massachusetts.
Stop and wander this cute little town and grab a bit to eat at the Spring Street Market and Cafe, then get back on the road for a scenic drive back to Boston along scenic Route 2.
Along the way, stop and admire the foliage in the hilly windy roads and Windsor Lake outside of North Adams and the views over the Connecticut River outside of Gill. Take your time on the drive back to Boston, admiring the foliage and tiny towns along the way!
While you could spend weeks exploring the Autumn colors of New England, start with an introduction weekend and this is a great itinerary to see as much as you can in a weekend of these beautiful States!