Hello friends,
And Hello August!! I can’t believe that it is already that time of the year, yet again. This is the time of the year that I actively start to plan out my fall trip. Leaf peeping in New England is a popular fall activity, and I am hooked. This will be my 8th year visiting. It has been such a memorable, relaxing trip that comes at the busiest time of the year for a sport’s mom. But, I have made it a non-negotionable.
If you have never visited this area during the fall season, add it to your wishlist and pin this post for later. You won’t regret it!!
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Where to begin:
1) I start with tracking the foliage map: HERE !!!! This is key so you can properly plan your trip when the foliage is peaking. So, don’t start booking your airfare, lodging, rental, and reservations until you know for sure what they are predicting. I have visited when the leaves weren’t as colorful, and it is a little disappointing.
2) Next, I check prices on airfare. It varies from day to day. Prices can jump to $1k during peak season. I try to book airfare under $500. And, I usually fly into Burlington. It has the best options and car rental options too. It is centrally located for the cities that I like to visit.
3) After airfare is booked, I secure my car rental asap.
4)Lodging is next, but before booking my lodging, I map out my itinerary. This varies each year based on who joins me on the trip.
I try to mix it up a little each year. But, I always include Stowe and Woodstock. From there, I have taken different routes. We loved visiting New Hampshire. And, we thoroughly enjoyed going south to Manchester, Dorset, and Bennington.
A few years ago, we added Boston, Martha’s Vineyard, and Rhode Island to the route too. It is all so beautiful. Below, I’m sharing my itinerary from last year.
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Day one – flew into Burlington:
We landed late so we didn’t book any reservations for dinner. We picked up our rental car, grabbed some fast food, and headed straight to our lodging at Field Guide Lodge in Stowe.
Stowe is roughly a 45 minute drive from the Burlington airport. This is my third time to stay at this lodge. I love the location and the larger suite options.
There was a mix up with our suite which was frustrating, but they sorted it out the next day. Also, I love that breakfast is included which is very nice.
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Here is a list of other favorite spots for lodging in Stowe:
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Day two – headed to Woodstock:
We woke up early to get a full day of exploring. We chose to drive an hour to Woodstock since it was the best weather on this day. Woodstock looks like it is straight out of a Hallmark movie.
We headed to The Village Butcher to eat lunch since we had a light breakfast. Y’all, they have the best sandwiches. After lunch, we went shopping, visited the Woodstock Inn, checked out the library, and enjoyed some maple ice cream.
Take your time, take pictures, and wander past the Middle Covered Bridge, Ardmore Inn, and Pleasant St. The fall decor on the houses is my favorite. Every inch of Woodstock is picture perfect and absolutely magical.
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After exploring, we decided to head back to Stowe. We had dinner reservations at the Cork. This restaurant is a 10/10. The food is always amazing, and I love the cozy yet lively vibe.
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More dining options in Woodstock:
Simon Pearce(out of the way but a beautiful view)
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Lodging in Woodstock:
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Day three – exploring Stowe and more:
We decided to explore Stowe and go to an apple orchard if we had enough time before dinner and lantern tour. But first on the agenda was going to Cold Hollow Cider Millto get the best hot cider and apple donuts.
This is a must every year. When I brought my parents to Stowe, we came here every day for hot cider and donuts. It can get crowded with tourist but worth it. Take some pictures and enjoy.
After this, we headed to the the Gondola SkyRide to ride the gondola up the mountain for the best views. We did purchase tickets weeks in advance, and you do need to check the dates of operation. They close mid October.
This is optional but a great experience. This year, they had snow on the top of the moutain which was really cool.
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Apple picking is something that everyone has to experience while in Vermont. I usually have to call a lot of local farms to see who is still has apples on their trees and open to visitors.
Each year, it is a different orchard. Chapin Orchard in Essex Junction is where we decided to go apple picking. It was so lovely and family owned since 1929.
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After this, we headed back to change for our dinner reservations at Swiss Fondue. This is a cozy restaurant with the sweetest owners. And to eat fondue on a cold night is just always perfect.
Stowe has so many amazing restaurants, but you definitely need to book reservations in advance for dinner. If you wait too long, the options are not as great. The same goes for all of the cities that you visit. S0, just make as many reservations as soon as possible.
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We ended the night with a Stowe Lantern Tour which is always so fun. This tour sells out quick and is only offered on certain days of the week so call to add your name to the list. The tour guide tells stories of the early settlers, the historic buildings, and more about the history of this town. We highly recommend.
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Additional dining spots in Stowe:
Plate ( my favorite dinner spot)
Cork Restaurant & Wine (another favorite dinner spot)
Butler’s Pantry (my favorite breakfast which is a must)
Piecasso (the best pizza)
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Day four – headed to Manchester:
We woke up to spend our last morning in Stowe before heading south to Manchester. Breakfast at the Butler’s Pantryis a must and is a long wait so go early. We added our name to the waitlist and went exploring on Main St. They have the cutest shops. Also, make sure to check out the Stowe Recreation Path. Walk to the Giles W. Dewey Memorial Bridge to get a beautiful view and great picture of the town of Stowe.
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After breakfast, we visited the three bridges that are famous in Stowe. Covered bridges are a classic staple in New England, and Vermont has over 100 of them.
Travelers visit from all over to admire and photograph the unique architecture and designs of these historic structures. Emily’s Bridge located at the intersection of Gold Brook Road and Stowe Hollow Road, Brookdale Bridge located at one end of the Stowe Recreation Path, and the Red Covered Bridge built in 1896 is located in Morristown.
And if you have time, Smugglers Notch is a scenic 3.5-mile mountain pass that is part of Route 108 between Cambridge and Stowe. It’s known for the beautiful scenery, steep cliffs, and winding roads.
I love to show my friends and family this picturesque and dramatic scenery.
After this, we headed to Manchester which is roughly 3 hours south. And the views on the drive were STUNNING!! It is something that I have never witnessed.
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Our lodging was at the Kimpton Taconic Hotel which did not disappoint. This is definitely my favorite hotel that I have stayed at while visiting Vermont. The faculty, the decor, the amenities were all a 12/10. They even had cute bikes for the guest to use while exploring downtown.
We took advantage of the bikes and went exploring. It was amazing. They have so many cute shops and the best bookstore. The hotel had an afternoon social for the guest with popcorn and wine on the front porch.
The vibes were definitely vibing.
We ended the night with dinner at the hotel which was lovely. And, we had a night recap by the hotel’s fire pit. It was thee best day.
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Additional lodging in Manchester:
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Day five – headed to Dorset & Bennington:
We woke up early and headed to the Dorset Bakery which was maybe 15 minutes from our hotel. This bakery was just dreamy. We had the best meal and took lots of pictures.
After breakfast, we headed to Old Bennington to visit some historic buildings and graveyard. We visited The Old First Church,the grave of Robert Frost, and the Bennington Monument which is the tallest building in the state.
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Next, we headed to the Shaftsbury Alpaca Farm. This is not something that everyone would enjoy, but Bella and I were ecstatic to meet each and every one of these cuties. We even bought some alpaca socks for the entire family.
On the way back to Manchester, we stumbled upon another apple orchard in Dorset, Mad Tom Orchard. Picked a few apples for our family and friends, and we enjoyed our last, hot cider.
We headed back to the hotel to change for dinner at the Dorset Inn Restaurant for our last evening in Vermont. Our meal was delicious. Highly recommend dining here.
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More dining suggestions in Manchester/Bennington/Dorset:
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Day six – headed back home!!
I do hope that this helps you plan the most epic, fall trip!! If I can help answer any questions, message me on Instagram or email me at angelle@dashingdarlin.com.
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