I had seen a small town continuously showing up on my instagram feed when we first moved here back in 2017 of amazing fall colors and a charming village town that I knew I had to check out in real life. In 2018 when we started getting settled in Connecticut, we started breaking out and doing lots of road trips – one of our favorites being going to the amazing state of Vermont in the fall. Vermont is about 3 hours from Connecticut (give or take where you live in the states) and is truly worth the drive alone for the beauty you will pass through! It’s no secret, New England in the fall is unlike anything you will see…anywhere.
Since our first trip back in October of 2018 we have made a bit of a tradition out of it by going back each year! These images and this guide will be based on our 2018 and 2019 fall trips to VT – which means more info and pictures for you to sift through when planning your dreamy fall getaway. We have made our way to Stowe and Burlington as well – but that will be a separate post on a different day! 🙂
Below is our suggested map if you are coming in from Connecticut. This would be a perfect long weekend trip or even longer If you are able. I would suggest 4-5 days to get a good feel for the area and to have time to meander and take your time…which is WHY you go to Vermont. To slloooow down!:)
Here is my suggested map if you are driving in from Connecticut. You can adjust as you like based on what State you are coming in from!
Day 1:
Head out early to beat the traffic and to get a start on your day. I suggest staying in the cute town of Chester, Vermont to experience beautiful countryside and all the small town charm.
Walk the old streets and meander through the sweet shops…you will find some great antiquing in Vermont as well (so keep your eye out!).
Food and Lodging in Chester, Vermont:
For Brunch I highly suggest the Country Girl Diner ! It’s such a fun place to go eat as it’s in a genuine vintage Silk City Silver Dining Car! The food is great and the atmosphere is lively. Also, be sure to get some pancakes or waffles so you can try the Vermont Maple syrup!
For dinner I suggest MacLaomainn’s Irish Pub ! It’s right off of Main Street and has great food and atmosphere if you love a good classic pub with great drinks and Irish food. If you have a sweet tooth, walk over to Southern Pie Company for a fresh slice of apple pie – I promise you won’t regret it! Another spot we really enjoyed was Ye Olde Bradford Tavern which is also the Fullerton Inn – a beautiful historic Inn that we highly suggest staying at for your night in Chester!
Day 2:
On your way out of Chester, your next stop would be the iconic Vermont Country Store in Weston, VT. Their are a few locations but you guys, this town will take you back to your childhood – or the idilic childhood you always wished you had! It smells like the holidays as soon as you enter the old wood building..a toy train will be above you chugging along the stores ceiling, you will find a vintage toy section, home decor, home goods, food, gifts, clothes…etc etc etc. Cameron and I fell in love pretty quick with this store because it truly was the perfect fall experience and exactly what you would hope to find on a trip to Vermont.
After you’ve had your country store fix make your way to beautiful Plymouth, Vermont to visit the Calvin Coolidge Homestead District which happens to be one of our National Parks! This is a stunning outdoor museum that is super fun for families and for anyone who loves history and the countryside. We were pretty blown away with the homesteads beauty and also enjoyed learning about President Coolidge’s history and ties to Vermont. I would plan for a few hours here for your visit. Please note that the homestead is open May – mid October.
Be sure and check out the Artisan cheese shop in the Homestead before you head out! We bought so many souvenirs from this store!
At this point it is probably around 3pm or so and it’s time to head to the beloved Woodstock, Vermont! It is about a 20 minute drive from here so you should get there just in time to settle into your lodging and get ready for dinner out in the town.
This charming small town looks like it’s right out of a Norman Rockwell painting…it’s what you think of when you dream of Vermont and seeing it during the fall will make you feel like you’re at Disneyland (but REAL!) because it’s that idilic and charming. If it’s your first time…get ready for all the pretty things – be sure and have your camera ready as I’m sure you will be snapping away!
Food and Lodging:
I would suggest staying 2 nights in Woodstock, VT. If you want to splurge a little – I would say the hotel you want to splurge at is the incredibly beautiful Woodstock Inn. I visit this hotel every trip and always stop to take lots of photos – It’s just amazingly beautiful and quintessential New England! Be sure to pop inside to take a look at the beautiful classic interiors and hotel shop!
A few other notable hotels to check out are the Blue Horse Inn and The Shire Woodstock (river front!).
For a nice dinner I suggest The Prince and the Pauper or for a more casual dinner head up the road to Worthy Kitchen for craft beer and a farm to table food!
Day 3:
For day three I suggest touring the small town of Woodstock and window shopping, There are so many cute shops! A few of my favorites are the Vermont Flannel Co, FH Gillingham & Sons, and The Yankee Peddler Bookshop.
A must see is the beautiful Gallery on the Green right next to the town crier. The owners are Chip (the artist) and Opal his wife. They are the kindest people and Chip does amazing work! You can often find him in the back painting. I also have to say that I just love their dog, Bear, who mans the shop! It’s a must.
Be sure and walk along the small streets to see the historic homes filled with character.
Don’t forget to take a photo by the Middle Covered Bridge!
The next thing you will want to do is head over down the road to Billings Farm and Museum. This farm is incredible and I think it’s a must do! It is a fully working historic farm that has tons of animals, history and land for you to roam on. It also is a place you just won’t want to leave…with incredible views to boot.
From here I suggest doing a little driving around the area to see the beautiful views and farms. Here are a few beautiful spots we found around the area and on our drive to here.
Day 4:
Today I suggest heading over to the town of Quechee! This is just 15 min or so away and another small sweet town to visit. First head over the the Quechee River Gorge! It’s especially stunning with the leaves are turning.
After this, head over to one of Cam and my favorite places – Simon Pearce! Explore the beautiful flagship store and glass blowing workshop. We love to meander through the shop and look at all of the custom glass blown pieces and pick a favorite each time to remember our trip by (Cameron swears by their whiskey glasses). It’s also really fun to go downstairs and see the artists creating and blowing glass!
Be sure and have lunch or dinner at the amazing Mill Restaurant at Simon Pearce – it’s one of the best spots to eat in the area!
From here we suggest driving 15 minutes north to Hanover, New Hampshire to visit Dartmouth University! I mean – what says fall like college IV league life?! The campus is stunning and there was so much going on when we skateboarded through the area. Live music, a marathon, students walking around. It was alive and fun and the trees were in full color. Be sure and stop by the cute town of Hanover to shop and grab some dinner – there are lots of options (hello, college town)!
Day 5
The time has come to head home! On your way out of Woodstock head the beautiful Farmhouse Pottery for a treat for your eyes! All of the pottery in the store has been made on site in the studio that you can actually walk into and watch the potters hard at work! We happened to go during an event and they had pie and a pizza oven food truck – so it made for some great pics that set the scene. 🙂
Your very last stop before you leave Vermont is an apple picking orchard with none other than (we think are the very BEST) apple cider donuts! We personally love Green Mountain Orchards in Putney, Vermont! It has beautiful scenery, tasty apples and orchards and a really cute farm shop.
Now back home to Connecticut to make some apple pie with all of those apples you just bought!
I hope you enjoyed your time in the beautiful Woodstock, Vermont area!
Tell me, where are your favorite spots to go in this region of VT?!
