Woodstock Travel Guide

It’s hard to play favorites in New England, but next to Rhode Island, Vermont is at the top of my list. It’s pretty wild to think when I wrote this travel guide three years ago I only dreamed of living there one day. I will never forget hopping on bikes we borrowed 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 snowy covered bridges and cross country skiing, or visit in the summer for lake swimming and lush green mountains. No matter the season, there’s plenty to enjoy. Here’s some ideas and suggestions for things to do, places to stay, and where to eat.

*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.

Jess Ann Kirby stops by the Woodstock Inn during her weekend getaway to Vermont
The Woodstock Inn

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 12/24/21-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 when we first visited in September. 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’ve stayed at this cabin super close to town and it was absolutely great. The only downside is that it’s not pet friendly. The owners were super responsive and accommodating, I would love to stay in this place in the winter! If you’re looking for a pet friendly rental, we also 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.

What to Do

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 the shopping, strolling, spa type or  adventurous and outdoorsy I can guarantee you will not be bored.


Farmhouse Pottery
The Vermont Flannel Company
FH Gillingham & Sons
Simon Pearce (great place to get lunch, shop and watch glass blowing downstairs)
Woodstock Sports
Clover Gift Shop
Danforth Pewter
The Yankee Bookshop
Woody’s Mercantile
Market On The Green – Woodstock’s Farmer’s Market every Wednesday from 3-6pm, June-October.

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).
Suicide Six – Mountain Biking, Skiing/Snowboarding
Aqueduct Trails – Mountain Biking, Hiking/Walking (great place to walk dogs!)
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.
Quechee Gorge – Hiking
Silver Lake – Swimming, Kayaking, Canoeing, Paddleboarding
Sugarbush Farm – Cheese and maple syrup farm.
Go for a Drive – Two scenic drives we’ve done that are absolutely breathtaking. I’ve linked to the directions for a few of them (both are pretty quick and easy from Woodstock).
Woodstock > Barnard > Killington > Bridgewater > Woodstock – 1 hour and 15 minutes (we stopped for lunch at Long Trail Brewing)
Woodstock > Quechee (via Happy Valley Road) – 20 minutes

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.
Kelly Way Gardens – An incredible farm to table dinner experience (also open to the public for tours during summer months).
Mon Vert Cafe – Great spot for coffee, pastries, breakfast sandwiches.
Long Trail Brewery – Yummy lunch spot.
Worthy Kitchen – Farm to table comfort food. It gets really busy, go early if you can.
Woodstock Farmer’s Market – Great place to grab quick prepared foods. They have an incredible grocery selection too if you need to stock up during your stay.
Simon Pearce Restaurant – We had a really nice lunch here.
Soulfully Good Cafe – Great breakfast spot!
Cloudland Farm
The Ransom Tavern at Kedron Valley Inn
The Prince and The Pauper
The White Cottage Snack Bar

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  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!


    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