Woodstock Travel Guide

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.

Jess Ann Kirby stops by the Woodstock Inn during her weekend getaway to Vermont | Woodstock Travel Guide
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 12/24/21-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 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’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.

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

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 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!

The Vermont Flannel Company – All your cozy flannel needs.

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

Simon Pearce – Great place to get lunch, shop and watch glass blowing downstairs (this is in Queechee)

Andrew Pearce – Beautifully handcrafted wood bowls, cutting boards and more. I’ve purchased many wedding gifts here!

Woodstock Sports – Local sport shop with a nice selection of clothing and gear.

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

Danforth Pewter – Lots of beautiful handmade gifts. Everything they sell, they make in Vermont!

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

Woody’s Mercantile – Fun unique items and gear.

Market On The Green – Woodstock’s Farmer’s Market every Wednesday from 3-6pm, June-October.

Wigren Barlow Art & Antiques – Adorable art and antique shop in town.

Eric Nesbitt Art & Antiques – Right next door to Wigren Barlow!

Vermont Antique Mall – This spot is actually located in Queechee not far from Queechee Gorge. It’s massive and a cool place to walk around and check out tons of antiques.


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

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 (dog friendly).

Silver Lake – Swimming, Kayaking, Canoeing, Paddleboarding

Sugarbush Farm – Cheese and maple syrup farm.

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

Scenic Drives

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. 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).

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, and lunch. Outdoor seating available.

Long Trail Brewery – Yummy lunch spot with outdoor seating (located in Bridgewater).

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.

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. Picnic tables by the river.

Woodstock Scoops – A new locally made ice cream shop in town. Check their website for hours, open seasonally.

Simon Pearce Restaurant – We had a really nice lunch here.

Soulfully Good Cafe – Great breakfast spot! Outdoor seating available.

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

The Prince and The Pauper

The White Cottage Snack Bar – Outdoor seating available.

Abracadabra Coffee– A super cute little coffee van at East End Park. Check their website for hours and location.

Cloudland Farm

Woodstock Travel Guide

Upcoming Events in Woodstock, VT

Kid friendly dining and activities

A few suggestions for dining and activities with kids:

  • Billings Farm – animals, lots of room to roam outdoors, demonstrations and fun fall activities
  • Sugarbush Farm – Maple syrup tasting
  • Marsh Billings Hikes – This loop and this one are the easiest for younger hikers.
  • VINS – Nature center with outdoor tails, a forest canopy walk and more.
  • Worthy Kitchen – Kids menu and picnic benches for casual outdoor dining.
  • Mon Vert – Kids menu and outdoor seating.
  • You can also take food to go and picnic at East End Park, Faulker Park (only 1 picnic bench here), or the Village Green.
  • There is also a playground behind the Woodstock Inn across from the Elementary School.

Dog friendly dining and activities

  • Mt. Tom – The park at the bottom (Faulkner Park) is dog friendly on leash.
  • Aqueduct Trails – Hiking and mountain biking spot. Dogs allowed off leash
  • Marsh Billings National Park -Lots of hiking trails, dogs allowed on leash. Park across the street at Billings Farm.
  • Quechee Gorge – Dog friendly hiking.
  • Worthy Kitchen – Picnic tables for outdoor dining with dogs
  • Mon Vert – Outdoor tables.
  • East End Park – Picnic tables and trails along the Ottaqueechee River for on leash walks.

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14 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