How To Spend a Perfect Day in Woodstock, Vermont

Woodstock, Vermont is a small town, which was named “ the quintessential New England village” and for good reason! Walking around Woodstock kind of feels like you’ve been placed on the film set of Gilmore Girls and you’re in a beyond charming, dreamy, rural fantasy land. Woodstock, Vermont is filled with beautiful, locally-owned shops, adorable cafes and restaurants, picturesque covered bridges, and stunning, historic 19th-century buildings.

On a recent girls’ trip to Vermont, we spent a full day exploring Woodstock and its surrounding areas. Every bit of Vermont that we managed to see over that weekend was mesmerizing, but Woodstock left a lasting impression on us.

If you’re planning a trip to Vermont I assume you’ve stumbled upon this post because you’re interested in including Woodstock in your itinerary. Or maybe you’re just considering it. Well, I’m here to tell you that Woodstock should 100% be on your Vermont must-visit list! I also want to share this guide on how to spend the perfect day there. In this post, I will have you covered with wonderful restaurants to eat at, the best places to take in the views, great tips for visiting Woodstock, and I’m even including a road map of the day. So let’s get to it!

For Other North America City Guides, Check Out These Blog Posts:

• The Ultimate Guide to Buffalo, New York
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• Things To Do in Ellicottville, New York During The Summer

Getting To Woodstock, Vermont

Vermont is a relatively small state and getting around is quite easy. The largest airport in Vermont is Burlington. Chances are if you’re flying, this is the airport you’ll be landing in. Burlington is in the north and right near the border of New York State. Here, we rented a car and did a little road trip down to Woodstock, which is in central Vermont. Not including any stops that we made along the way (also just to mention our accommodation was about 30 mins outside of Woodstock in a town called Pittsfield) the drive from Burlington to Woodstock is just about 1 hour & ½.

If you’re driving, I’m sure there will be a point in time where you find yourself on Vermont Route 100. This is Vermont’s most scenic drive! It runs through the center of the state, north to south, and there are plenty of picturesque places to stop along the way.

Tip #1:

While on your way to Woodstock, keep a lookout for spots on the road that you can stop off. The drive has many twists and turns so areas to stop off come up very quickly. But, if you happen to see an extra-large shoulder on the road, it’s totally worth it to pullover (ONLY WHEN IT’S EXTREMELY SAFE TO DO SO) and really take in the scenery. 

How to Start off Your Day

First things first, any day in a new town or city should start off with a fantastic meal! Woodstock is filled with tons of cute cafes offering up great breakfast and brunch menus. Take a stroll down Central Street and consider having your first meal at one of these amazing places:

Mon Vert Cafe

Mon Vert was our very first stop once we arrived in Woodstock. We realized that everyone in town had the same idea as us when we noticed the line down the block. Mon Vert is an extremely popular cafe serving up breakfast & lunch dishes prepared with organic, local ingredients. They are also very passionate about their coffee! Unfortunately, we were a little too hungry to wait for the line to die down so we moved on. However, if you manage to reach Woodstock on the earlier side and can get in before the crowd, I’ve heard that Mon Vert does not disappoint. They are open Friday- Wednesday 9 am- 4 pm and you can access their menu here.

Soulfully Good Cafe

Since we struck out with plan #1 we moved onto #2, which was just a short walk down the road. Soulfully Good Cafe is a very cozy, welcoming place with a cute outdoor patio as well as indoor seating. They serve breakfast every day until 11:30 am and then they move onto their lunch menu which is served until 3 pm or 4 pm, depending on the day. We unfortunately just missed the cut off for breakfast but were happy with their simple, yet delicious lunch menu filled with salads & paninis. We were still in a brunch mindset though so we added on a couple of rounds of mimosas too! Initially, we were a bit disappointed that we didn’t get to eat at Mon Vert, but we couldn’t have been happier with Soulfully Good! Check out their menu here.

Where to Spend Your Afternoon in Woodstock

After you’ve gotten in your first meal of the day it’s time to do some exploring! Continue your stroll down Central Street. There are plenty of adorable shops worth stopping in and depending on what time of the year you visit, the storefronts are all festively decorated and very cute!

Tip #2:

The best time of year to visit Woodstock is during the fall months, specifically when the foliage is at its peak. This varies year to year but generally, you’re looking at the end of September to mid-October. During this time the town is all dressed up with pumpkins and festive autumn decor. You also just cannot beat the natural beauty that Woodstock offers during this season! There are many destinations out there that I would recommend visiting during the offseason, but Woodstock is not one of them.

While wandering around town, there are a couple of specific places I would recommend checking out:

Woodstock Middle Bridge

Vermont is quite well-known for all of its covered bridges- to be more precise, there are over 100 of them! Some of them date back to the 1820s but most were constructed from the mid to late 19th century. Just off of Central Street you will stumble upon Woodstock Middle Bridge. This is a beautiful, wooden covered bridge that will have you imagining that you’ve laid your eyes on a painting. A great feature of Middle Bridge is that there is also a path for pedestrians wanting to walk over and the views are stunning! This area can get a little congested between tourists (like myself) wanting to take photos and cars wanting to actually use the bridge for its intended purpose, but with a little patience, it was easy to have the place pretty much to ourselves.

Teagle’s Landing/ Kedron Brook

While walking down Central Street you will discover a set of wooden stairs that leads down to a river. This is Kedrom Brook. You’ll know you’re in the right place when you see the sign “Teagle’s Landing”. This small oasis is named in honor of Frank H. Teagle, Jr. who was a Woodstock resident from 1945 to 1997. He was a thoughtful and selfless man who worked to make his community a better place. This lovely area has been dedicated to him. It’s such a beautiful little piece of nature running right under a buzzing street. Take a walk down here to enjoy it for yourself.

Check out These Super Cute Shops

As I’ve mentioned before, Woodstock is filled with tons of cute shops! And if you’re strolling down Central Street you’ll have no choice but to walk passed them so you might as well stop inside. I would definitely recommend checking out Yankee Bookshop. This is Vermont’s longest-running independent bookstore, which opened in 1935! They have books, vinyl, stationery, and gifts. Then there’s F.H. Gillingham & Sons which has tons of great quality local products such as maple syrup, cheese, macaroons, honey, and so much more. Lastly, Red Wagon Toy Co. is an adorable shop and a great place to buy gifts for any little ones in your life. A friend that was on this trip with me just had a baby six months ago and this place was perfect for finding something to bring back home to her.

Exploring The Surrounding Areas of Woodstock, Vermont

After taking the time to walk around town and enjoy the literal charm in the air that Woodstock gives off, it’s time to explore out a little bit further. All of these stops are within a 15-minute radius of Woodstock and I would highly recommend all of them!

Billings Farm & Museum

Billings Farm is not just a working farm, but it’s also an extensive museum dedicated to scientific farming history. Located just a short 2-minute drive outside of town, you’ll experience the beautiful Vermont countryside here at Billings Farm. Through their tours, they offer diverse, interactive programs that focus on rural life, traditions, and values dating back to the 19th century. If you’re interested in discovering more about Vermont’s rural history, this is a great place to start. If you’re not interested in taking a tour Billings Farm is still a beautiful place to see Vermont’s scenery, enjoy the autumn foliage and even spot a couple of cows.

Jenne Farm

A 17-minute drive from Billings Farm will bring you to Jenne Farm, which is not only the most photographed farm in Vermont but in all of North America. Let me just tell you right now, it is beyond gorgeous! You’ll enter a dirt road that is technically two-way but you’ll wonder how two cars are meant to drive down it at the same time. I’d recommend parking a little ways from the farm and walking the rest of the way to take in the scenery. The rolling hills, beautiful valleys of green, and outstanding colors of the changing leaves will leave you absolutely breathless!

Tip #3:

Jenne Farm is a private residence so always be respectful when walking around and taking photos of the property. It obviously doesn’t cost anything to visit Jenne Farm, but there is a donation box on the premises.

Quechee Gorge

About 15 minutes east of Woodstock is Quechee Gorge. This one we stumbled upon by mistake and it ended up being one of my favorite parts of the trip. We were seeking out a winery and my google maps led us to Quechee Gorge Village- a connection of different antique and souvenir shops, homemade fudge, a grocer with local products, and a little corner where wine is sold. (Not exactly the winery we had in mind) On the left-hand side of Quechee Gorge Village is an adorable Alpaca Farm and just over the bridge is “the” Quechee Gorge, a sight absolutely worth seeing! It’s one of those views that are completely untouched by mankind and have seemed to remain just as mother nature intended it to. What do you think?

Finishing off Your Day

After a full day of taking in the sights and exploring a beautiful, new place, it’s time to end the day with another delicious meal. Woodstock isn’t short of amazing places to eat and I’m going to share some wonderful recommendations with you:

Tip #4:

If you can, make dinner reservations! I’m assuming it’s because we visited during the peak time of the year but every restaurant we walked into had anywhere from 30 minutes to over an hour wait. We even went to dinner on the earlier side (before 5 pm) thinking it would make a difference but it did not! Make reservations and avoid the hassle. 

Cloudland Farm

Dining at Cloudland Farm was our first choice and I really dropped the ball on this one. I should have called for reservations weeks in advance and it was one of those things that just slipped my mind. Of course, the evening that we wanted to have dinner there, they were completely booked out. However, if you plan ahead a little bit better than I did, having dinner at Cloudland sounds like the way to go. They offer up a true farm-to-table dining experience with a rotating tasting menu and beautiful countryside views. Check out their website here.

Worthy Kitchen

Worthy Kitchen is just a short drive outside of town and is a very popular spot amongst locals and visitors alike. They are all about craft beer, delicious, local food, and most importantly, creating a community. Check out their menu here.

Dr. Coburn’s Tonic

Dr. Coburn’s is a cute spot right in town and this is where we actually ended up. They don’t have a super extensive menu, but there’s a little something for everyone. Their cocktail list was great and had some delicious seasonal options. We started off with the chicken wings which were very good and if you’re a fan of wings I would definitely recommend trying them in Vermont. Most places offer a really tasty maple syrup-hot sauce blend, which is an incredible mix of sweet and spicy. This is a perfect restaurant to eat at if you’re finishing off your evening right in town and want to go somewhere walkable and cozy. Check out their website here.

I Hope Woodstock, Vermont is as Good to You as it Was to Me!

As I conclude my perfect day in Woodstock, Vermont guide, I would also like to share with you the road map of our day in case you would like to follow along a similar route! Please see the screenshot just below. I hope this guide has given you some inspiration and ideas for planning your own trip to Woodstock and if and when you make it to this incredible town, I wish you the very best time. Please feel free to leave any questions or comments below and as always, happy travels!