Best Fall Trip to the North East

Apple pickingRecently, my dear friend Whitney and I went on a girl’s trip to Boston and onto Vermont. This trip was the ultimate fall leaf peeping adventure. We couldn’t take too many days off of work so we put as many fall activities as possible into 3 days. In this post, I am going to share with you where we went, what we did, and what I do differently for the best fall trip to the North East.

We started our trip by flying into Boston and meeting up. (For context, Whitney lives in Texas and I live in Florida.) We rented a car at the Boston airport which was essential since we drove up to Vermont. We spent the first night adventuring in Boston before starting the drive up to Stowe, Vermont.




I loved Boston. This was my first trip to Boston. The crisp fall air was a nice change compared to the Florida humidity. We stayed at AKA Back Bay. I really like the vibe of this hotel along with the location. We were a quick uber away from North End which is where we spent the evening.Modern Pastry Boston

Due to my lack of research ahead of time, we weren’t able to get a reservation at the hottest Italian spots. Mama Maria and Carmelina’s came highly recommended and will be on my agenda for my next Boston visit. The dessert hot spot in the North End is Modern Pastry. We grabbed desserts at Modern Pastry and LOVED it! It is cash only with a wait, but absolutely worth the wait if you have a sweet tooth like myself.


The next morning we left Boston to head to Stowe, Vermont. The route we took was longer than the route apple maps suggests, but had better fall foliage which was the whole reason for the trip. On our drive to Stowe, we took part of route 100 & 106. Our first stop along the drive to Stowe was at Wellwood Orchard to go apple picking and create our fall content. I had a blast creating content with my bestie in the apple orchard (call me basic), but if content creation with your bestie is your vibe… I highly recommend apple picking.


As we continued along our drive, we stopped in Woodstock for a late lunch. (There aren’t a-lot of options on Monday and Tuesday for food especially outside of normal lunch hours in Woodstock so be prepared if you’re planning a lunch break in Woodstock.) I thought Woodstock was a super cute town that also would be a fun stay for a fall trip. Woodstock had an adorable downtown, and was closer to Boston than Stowe. If you are driving from Boston and don’t want to drive as far as Stowe, Woodstock is a great option.


After Woodstock, we continued our drive to Stowe where we stayed at the Stone Hill Inn. This inn was adorable! It was a little outside of Stowe, but its the perfect place for a girl’s trip or a couple’s trip. The inn was decorated beautifully, breakfast was served everyday, adult only and plenty of activities were available at the inn if you were looking to have some quality time in the evenings.


Must do activities In Stowe and the surrounding area

We had a blast in Stowe. It felt like we were living in a Hallmark movie. Since we only had a couple days we fit in as much as we could before driving to Burlington and fly home.

If you’re planning a trip like this, here would be my suggestions for creating the best fall trip to the Northeast.

  1. Timing: September 29- October 10 is prime leaf peeping according to the locals. I would recommend this trip be a 4 or 5 day trip so you can fully experience everything.
  2. Drive from Boston to Stowe
  3. Book dinner in Boston at one of the Hot Spots I recommended above for Italian followed by Modern Pastry
  4. Try as many of the activities as you can in Stowe

I hope these recommendations help you if you are planning a fall trip to the Northeast.

As always, thank you for reading! Please reach out with any questions.




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Madison Dorenkamp

Entrepreneur, podcaster, and blogger

Welcome to the Striving for Balance Blog! I created this blog for every girl who is striving to be her best while balancing her busy life.

Madison Dorenkamp

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