Search here...
TOP
North America Travel

Fall in Vermont: Road-trip Guide and Itinerary

Fall in Vermont - Road-trip Guide and Itinerary | fall foliage, New England travel guide, fall fashion and outfit inspo, aesthetic fall photos

Vermont is one of the most beautiful states to visit during fall. Three quarters of the state is covered in forest, so autumn is extra special there – as fall starts to creep in, all the leaves are magically painted in golden shades of yellow, orange, and red and everywhere you turn is bursting with color! There’s apple picking, pumpkin patches, covered bridges, and all the fall activities you can possibly think of. Fall in Vermont is definitely a bucket-list experience!

Here is my Fall in Vermont: Road-trip Guide and Itinerary


PEAK FALL FOLIAGE

Catching the perfect fall colors can be kind of tricky because the colored leaves transition very quickly and it’s not always so predictable, every year is different.

Because fall foliage attracts a lot of tourism, you basically have two options: book flights and lodging last minute at higher prices so you can arrive closest to peak OR you can plan and book ahead of time and save yourself some money but risk the possibility of missing peak.

My boyfriend and I happened to get lucky, we booked about one month in advance and we ended up arriving right on time on the first week of October! However, there is a super helpful New England fall foliage tracking map that you can use to help you choose your travel dates.

Once we decided on our travel dates, we booked our flights with Southwest Airlines and flew to Boston, Massachusetts. There we rented a car with Alamo (I made a reservation beforehand through Skyscanner.com) and began our road-trip.


DAY 1 – SALEM

Salem is a cute little town, only 30 minutes away from Boston, and popular for its witch history and for the filming locations of the iconic movie, Hocus Pocus. We decided to make a stop in Salem because we absolutely love Halloween and spooky things! Plus, we visited in October and that’s when the town comes to life!

WHAT TO DO IN SALEM:

WHERE WE ATE:

  • The Ugly Mug Diner – everyone was super friendly and we met some nice locals that were extras for Adam Sandler’s new Netflix movie!
  • A & J King Artisan Bakers – the best coffee & pastries
  • Howling Wolf Taqueria – the yummiest Mexican food, we fell in love with their spicy salsa!

Check out my blog post on 7 Fun Things To Do in Salem, Massachusetts!


DAY 2 & 3 – MANCHESTER

We then drove 3 hours to Manchester and completely fell in love with it! It is the most charming little town at the foot of Equinox Mountain so the town’s backdrop is absolutely stunning!

WHAT TO DO IN MANCHESTER:

  • Mt. Equinox Skyline Drive
  • Equinox Valley Nursery
  • The Lincoln Family Home
  • Emerald Lake
  • Lye Brook Falls
  • Walk around and explore the town
  • Drive 10 minutes over to Dorset

WHERE WE ATE:

  • Little Rooster Cafe – delicious breakfast food in a cute little country styled cottage
  • Charlie’s Coffee House – a coffee shop inspired by the cutest doggy named Charlie, and they serve the best lattes!
  • Thai Basil – we love Thai food and this spot did not disappoint!
  • Christos’ Pizza and Pasta – still salivating over this pizza! I just have to say…WOW!

WHERE WE STAYED:

We stayed at the cutest little Airbnb, 10 minutes north of Manchester. Everything was pretty booked so we had to stay a bit outside of town but we didn’t mind at all because the drive and scenery were mesmerizing!

You can get up to $65 off your next Airbnb stay by using my code!

Fall in Vermont - Road-trip Guide and Itinerary | fall foliage, New England travel guide, fall fashion and outfit inspo, aesthetic fall photos

DAY 4 pt.1 – WOODSTOCK

Woodstock was not in our plans, it was a very spontaneous decision after talking to our Airbnb host and learning that Woodstock was a local’s favorite! We drove 1.5 hours north of Manchester to visit this town for half the day. Once we arrived, I seriously could not believe my eyes! I instantly fell in love and it is possibly my favorite town that we visited! I highly suggest Woodstock!

WHAT TO DO IN WOODSTOCK:

  • Walk through Middle Covered Bridge
  • Visit Sleepy Hallow Farm
  • Visit Sugarbush Farm
  • Explore the town by foot

WHERE WE ATE:


DAY 4 pt.2 – SALEM & BOSTON

We drove 2.5 hours back to Salem after our half day in Woodstock because we still had so much we wanted to explore in Salem before returning home. After Salem we drove back to Boston, Massachusetts to meet up with some friends for dinner!

WHAT TO DO IN BOSTON:

  • Walk around Beacon Hill
  • Stroll through Boston Public Garden
  • Visit Isabella Stewart Garden Museum

WHERE WE ATE:


Looking for more road-trip adventures? Check out my 4-Day Road-trip Through Southern Oregon blog post!


TIPS FOR THE PERFECT AUTUMN ROAD-TRIP

  • Please make sure to get tested for COVID- 19 before any travels! Drugstores like Walgreens and CVS offer free testing.
  • Don’t forget to wear your mask whenever you’re in public!
  • Rent an economic car so you can save on fuel since you’ll be doing lots of driving!
  • Road-trips like these are always more enjoyable when you have a sense of spontaneity! Make sure you don’t get fixated on a particular plan if it doesn’t work out. Instead, go open-minded and live in the moment!
  • Download any maps/routes that you’ll need for your road-trip ahead of time because you might loose signal along the way.

PIN FOR LATER!


I hope you enjoyed my Fall in Vermont: Road-trip Guide and Itinerary! comment below if Vermont is on your bucket-list!

cindyycheeks

«

»

Leave a comment

Let’s Be Friends