A Weekend Getaway to New England in the Fall

New England, steeped in rich history, stands as a living museum showcasing a pivotal era in American heritage. The region’s significance traces back to the Colonial period, boasting historic towns, iconic landmarks, and cultural sites that narrate the story of the nation’s founding. Beyond its historical charm, New England entices travelers particularly in the fall, transforming into vibrant hues that showcase the beauty of the season. The viewing of fall foliage, known as “leaf peeping,” draws countless visitors every year, offering a visual symphony of reds, oranges, and yellows, as the landscape becomes even more picturesque.

For tourists, a visit to New England in the fall is an immersion into a quintessential American experience. Embarking on scenic drives along the meandering roads, such as the Kancamagus Highway in New Hampshire or Vermont’s Route 100, reveals a breathtaking panorama of colors. A stroll through quaint towns and villages provides an opportunity to engage with local culture, sample authentic cuisine, and discover charming boutiques offering handcrafted goods. Exploring iconic landmarks like the Portland Head Light in Maine, covered bridges in Vermont, or historic sites along the Freedom Trail in Boston, Massachusetts, allows for a deeper understanding of the region’s historical significance.

Engage in quintessential fall activities, from apple and pumpkin picking on picturesque farms to savoring warm cider and indulging in delicious seasonal treats like apple cider donuts. Hiking through state parks and nature reserves enables travelers to immerse themselves in the vibrant landscapes. The region also hosts a variety of fall festivals and events, celebrating everything from music and arts to harvest traditions, creating a lively atmosphere and offering a chance to mingle with locals.

Here’s everything we did while we were in Maine, New Hampshire, and Vermont from October 13-15th!

Our adventure began on October 12th around midnight when we touched down at Boston Logan International Airport (BOS). We were buzzing with excitement for our fall foliage-filled weekend! After we picked up our rental car, we hit the road and headed to South Portland, Maine to our hotel. It was a bit late, but the Casco Bay Hotel, which is part of the Ascend Hotel Collection by Choice Hotels, was a lifesaver with its ability to let us have a late check-in!

Waking up on October 13th, we were stoked to explore Portland, Maine. First up was the iconic Portland Head Light, and it was just as impressive as we’d heard. But let me tell you, the real treat was the lobster rolls from Bite into Maine with the ocean and lighthouse as our backdrop. It was like something out of a movie! We got to try the Connecticut and Maine-style lobster rolls, a whoopie pie, and Root Beer and Blueberry Soda from Maine Root! Everything was delicious and I really recommend paying this area a visit.

After that, we hit the road along New Hampshire 112, which is the Kancamagus Highway, where the fall foliage was absolutely breathtaking. We did our best to make a few stops along the way to enjoy all those colors! We spent a lot of our morning and afternoon in Maine, so our time in New Hampshire was short chasing the sunlight.

We stopped at Common Man for dinner in Lincoln, New Hampshire, It was well worth the hour-long wait! We had a Maple Whiskey Sour, Almost Escargot, New England Pot Roast, and a Nantucket Pie. The atmosphere inside was warm and cozy with the fireplace! After dinner, we finally headed to our hotel in Rutland, Vermont for a two-night stay at the Hampton Inn.

We stopped at Sugar & Spice (I just had to!! Petite and Spice made a visit to Sugar and Spice) for breakfast where I ordered coffee and the classic sugar and spice pancakes with real maple syrup. We visited the gift shop before we left and picked up a few souvenirs!

We then made our way to Woodstock, Vermont — We visited the covered bridge, in downtown Woodstock, had a maple creemee, and visited the cute white picket fence with mini pumpkins on Pleasant St.

We then paid a much-needed visit to the Cold Hollow Cider Mill in Waterbury, VT. They had apple cider donuts and hot apple cider and we couldn’t resist trying the hard cider flight in their tap room! I definitely drank mine a little too fast, but everything was delicious. We wanted to find a place to eat in Stowe, but with it being close to the end of peak season, everything was packed and needed a reservation. We actually just headed back to our hotel and enjoyed some pizza in while we watched a movie.

Our last day was Sunday and we had to say goodbye to Rutland, Vermont. But before we left, we just had to make one last stop at Last Cup Cafe in downtown Rutland, VT for a quick coffee and bite to eat. With our hearts full of memories from this fantastic fall foliage weekend, we headed back home. I’ve got to say, this trip left us both yearning for more New England adventures in the future! I wish I was here longer, but I had to make it back in time for work on Monday… Next time I’ll spend more time in all the historic places, specifically more time in Boston, experiencing breathtaking views, and trying more New England foods.


Now, if you’ve been to or live in New England and have a favorite spot, I’m all ears! Share your recommendations and I’ll add them to my growing travel list. Can’t wait for more adventures ahead! 🌲🍁🚗💨



  1. Taylor says:

    Love your vest outfit! New England in the fall sounds like a great time.

  2. Katelynn Kellogg says:

    I haven’t made it to that part of the East Coast just yet so I’m glad you were able to share it with me through your beautiful photos!

  3. Jenn says:

    There is no place like New England in the fall! Driving the Kangamangus Highway is iconic and I loved our time in Woodstock..great recs!

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