Woodstock Travel Guide

By Jess
6 Dec 2021

It’s hard to play favorites in New England, but Vermont is at the top of my list. It’s pretty wild to think when I first wrote this travel guide three years ago I only dreamed of living there one day. I will never forget hopping on bikes while staying at the Woodstock Inn and riding through town. Craig and I stopped on a little side street, looked at each other and said “we need to live here.” We are usually always ready to head home at the end of a trip, but Vermont was different.

Driving along winding country roads, passing farms and covered bridges, it’s a place that feels suspended in time. It felt like home. Forget strip malls, big chain stores, and billboards, what you’ll find in and around Woodstock is good old New England charm. Not only is it absolutely beautiful but the people are the ones that make Vermont special. Incredibly friendly, warm and welcoming, Vermonters greet you with kindness and a sense of community.

Visit in the fall for the most spectacular shows of fall foliage, come in the winter for snow covered bridges and cozy days by a fire, or visit in the summer for lake swimming and lush green mountains. No matter the season, there’s plenty to enjoy. Here are some of my favorite things to do, places to stay, and where to eat when visiting Woodstock, VT.

*A general note. State regulations and recommendations are constantly changing and evolving due to Covid-19. Please follow all state and local mandates when traveling and enjoying time in Woodstock and the state of Vermont.

Woodstock Inn | Click. Read. Love. 5.13.22
The Woodstock Inn

Woodstock Travel Guide

Where to Stay

Our first visit we stayed at the Woodstock Inn which is one of the main reasons we fell in love with Woodstock (book with this link to get 10% off your stay until 12/24/22-holidays are blacked out). You can’t beat the location which is set right in the heart of Woodstock, easily walkable to everything in town. The rooms are comfortable and charming, and they have several that are pet friendly! There are several dining options on site, but if you happen to be visiting when Kelly Way Gardens is open it’s a must see. It’s a farm to table dinner that Craig and I had the chance to experience in September a few years ago. The meals are all created with food grown at the Gardens or local farms and the entire property and space is beautiful.

The Woodstock Inn also has an incredible list of amenities.

The spa is not surprisingly one of the most popular. I’ve had the opportunity to do several treatments and a mani/pedi and they were all wonderful. There’s also a heated outdoor saltwater pool for the summer months at the hotel. There’s an indoor pool at the Athletic Club open to Inn guests. The Athletic Club is an amazing facility with indoor tennis courts, a gym, outdoor tennis courts, fitness classes, sauna and steam room. It’s my favorite place in the winter months for tennis and swimming. Not far from the Woodstock Inn is the Woodstock Country Club a phenomenal course designed by Robert Trent Jones. In the winter months it turns into a nordic skiing and fat biking track.

Woodstock Inn also offers a fly fishing program for guests. There’s truly so much to do in and around Woodstock. Skiing and snowboarding in the winter is so fun, with two mountains 15-20 minutes from the hotel. I can’t say enough good things about the Woodstock Inn (book with this link to get 10% off your stay until 12/24/21-holidays are blacked out).

If you’re looking for a rental, we stayed at this house on Silver Lake (about a 15 minute drive to Woodstock) and it was wonderful. You can rent the entire house or the main level upstairs and the downstairs apartment. It’s pet friendly too!

Click. Read. Love. 9.10.21 | Where to stay in Woodstock
THE SPA At the woodstock inn

What to Do (Top 20 Things To Do In Woodstock)

There really is no shortage of things to do in Woodstock. If you’re staying at the Woodstock Inn they provide plenty of bicycles to ride around town. There is plenty of great shopping and sightseeing which is all easily walkable. Whether you’re shopping, strolling, headed to the spa or going on an outdoor adventure I can guarantee you will not be bored. If you scroll all the way to the bottom, I’ve noted some kid and dog friendly activities and excursions as well as some upcoming fun events in Woodstock. I’ll update these seasonally!

Shopping

Farmhouse Pottery – The famous Farmhouse Pottery (as seen all over my house and kitchen, lol). Their shop and studio is a must see!

FH Gillingham & Sons – A Woodstock staple, part general store, part gift shop, they have a little bit of everything

Clover Gift Shop – Cute local gift shop with everything from blankets to candles and tea towels.

The Yankee Bookshop – Adorable book shop right in the center of town.

Woody’s Mercantile – Fun unique items and gear.

Hikes & Activities

Mt. Tom – There are a few different trail options to hike to the top. We did the Faulkner trail but there were some detours (clearly marked). The park at the bottom (Faulkner Park) is dog friendly on leash.

Suicide Six – Mountain Biking, Skiing/Snowboarding

Mt. Peg Trails – Mountain Biking, Hiking, Nordic Track/Snowshoe/Fat Bike in winter, no dogs during winter months

Billings Farm & Museum – Walking distance from the village. You can tour the barn, exhibits, and farm manager’s house and walk the grounds. No pets allowed at Billings Farm.

Marsh Billings National Park – Across the street from Billings Farm. Lots of great hikes, dogs allowed on leash.

Sugarbush Farm – Cheese and maple syrup farm.

VINS Nature Center – A nature center with raptors and songbirds, nature trails and a forest canopy walk.

Where to Eat

Mangalitsa – One of the best meals we’ve ever had. Farm to table. Intimate dining experience. Reservations only (we got SO lucky and got a table as walk-ins, it was 5pm).

Village Butcher – The BEST sandwiches we LOVE their Veggie Lover’s Delight. Grab it to go and eat it at Faulkner Park (there’s only one picnic table) or walk to East End Park and sit on the Ottaqueechee River (lots of picnic benches).

Mon Vert Cafe – Great spot for coffee, pastries, breakfast sandwiches, and lunch. Outdoor seating available.

Worthy Kitchen – Farm to table comfort food. It gets really busy, go early if you can. Outdoor seating available on their porch and you can also get takeout and sit at their picnic tables under the trees.

The Ransom Tavern at Kedron Valley Inn – So cozy and quaint. Yummy menu and fun cocktails. Outdoor seating available.

South Woodstock Country Store – Serving breakfast and lunch. Yummy sandwiches, salads and baked goods.

The Prince and The Pauper

Get the newsletter
Exclusive content filled with my favorite items, personal takes, and more.

Leave a comment

This site uses Akismet to reduce spam. Learn how your comment data is processed.

19 Comments

  1. Brittany L Cerminara wrote:

    VT is truly the best! Leaf peeping season is so fun too! Glad you enjoyed your visit.

    10.15.18 | Reply
  2. Rach wrote:

    OMG it is so cute there! I’ve heard people talk about Woodstock, but your photos definitely painted the perfect Fall scenery!

    http://www.rdsobsessions.com

    10.15.18 | Reply
  3. I love it when I see people visiting Woodstock! My Opa, Aunt and Uncle all live there and we try to visit once a year. We ALWAYS go to The White Cottage when we visit, more as a tradition than anything else. It sits right on the river and actually had to be rebuilt after the major flooding that happened a few years back. Before I even started reading your post I got stopped by your feature image. You can see my Opa’s house from that view on Mt. Tom so I had to find it before I could read obviously!

    Glad you enjoyed your trip!

    10.16.18 | Reply
    • Jessica wrote:

      Oh how nice. It is such a special place. All around the area is beautiful too. I love it there.

      10.24.18 | Reply
  4. Lynn wrote:

    OMG I just really want to be there right now! Insane longing. I had a flood that was cleared up from the air conditioner pipe in just 3 rooms and insurance covered it and did everything. I got home last week , went to bed and in the morning stepped into the kitchen on to 6 inches of accumulated water. We have not even found the leak as yet but we are back in a cute condo. Not sure how much good paper I’ll lose or wood flooring plus the mental anguish . Staying at my friends cute condo. I would love to safely get to Vermont right now . What a dream come true for you both. Sending love and I’m sooo excited for you guys!!! xoxo

    9.18.20 | Reply
    • Jess wrote:

      Oh no I am so sorry Lynn. How stressful, that’s the last thing you need. Hopefully you can get up to Vermont when it’s safe again.

      9.19.20 | Reply
  5. Jessica Camerata wrote:

    Dying to visit more of this part of the country. I’m just blown away by how picturesque it all is!

    xo Jessica
    an indigo day

    6.24.21 | Reply
    • Jess wrote:

      You would LOVE it. Come in the fall, it is spectacular.

      6.24.21 | Reply
  6. Hayley wrote:

    Oh this sounds amazing! I’ve spent the last ~6 months daydreaming and planning all sorts of trips in my head in quite a lot of detail, especially considering most overseas travel is currently next to impossible for we NZers. VT is going to be tacked on to my ‘New England up to Nova Scotia’ dream. ?

    When I lived in New York we made several trips to VT – snowboarding in Stowe and so he could race in a bike race in Killington – we were just reminiscing about them the other day and how amazing they were! This is very good timing. There was one bakery in Killington that did the *most amazing* espresso chocolate bread puddings and I would be very interested in seeing if it’s still there!

    6.24.21 | Reply
    • Hayley wrote:

      Um ‘he’ is my husband, reading back my comment I sound slightly deranged. It’s 6am for me so please forgive that!

      6.24.21 | Reply
      • Jess wrote:

        Haha! I got it. That sounds so fun. I’m going to need to find that bakery in Killington, we aren’t far from it!

        6.24.21 | Reply
        • Hayley wrote:

          I can’t remember its name and this was about 7 years ago but I so hope it is still going strong!

          6.25.21 | Reply
  7. Katie wrote:

    Gosh I love it up there! I’ve been going to Quechee & Woodstock since I was a baby and now love bringing my own babies there. Your list has all my favorites! The treetop walk and spider web at VINS is amazing. There is also a great playground in Quechee along Lake Pinneo with picnic tables for lunch or an early dinner. Two more shout outs:

    Chef Brad’s Crazy Side food truck: open seasonally (spring thru mid October I think), funky and delicious.

    Antique’s Collaborative on Route 4 in Quechee (before the Quechee Gorge) has some pricey but really incredible and special pieces.

    9.29.21 | Reply
  8. Jessica wrote:

    There’s just really nothing like fall in Vermont. Remember going as kids and the red leaves are so vibrant, like nowhere else. Need to do a trip back and all of this looks amazing!

    xo Jessica
    an indigo day

    9.29.21 | Reply
  9. Molly wrote:

    Wondering why you didn’t mention Ice Castles? Too obvious maybe? Too sold out? That’s my problem – we’re meeting friends for a weekend in the area and had REALLY hoped to get tickets. Alas, every timeslot is sold out. I’m sure we’ll find other things to do – thanks to your list! Next time, we’ll have to plan farther than a month in advance I suppose 🙁

    1.25.22 | Reply
  10. Thank you for sharing a travel guide in Dubai. These tips are very much useful to me.

    3.3.22 | Reply
  11. Chuck wrote:

    I prefer this blog because it has much more informative stuff.

    4.14.22 | Reply
  12. Rachel wrote:

    Thanks to this post, my family is thinking of visiting Woodstock over Memorial Day Weekend. A few questions for you as someone who lives in Woodstock with a little one! First, would you consider Woodstock Inn to be family friendly? We have a 2.5 year old, and I am always super conscious of his early morning noisiness when staying in a hotel. Second, any suggestions on hiking with a toddler? Specifically, ways to get them to do it (ha!) or trails that are wide enough to accommodate a jogging stroller?

    4.27.22 | Reply
  13. Sergio Brandao wrote:

    Hi Jess how are you?
    I need an tour guide on October 10 are you available? If you are please call me 917863-9173 thank you

    9.19.22 | Reply