Woodstock Travel Guide

Jess Ann Kirby hiked to the top of Mount Tom during her visit to Woodstock, Vermont

It’s hard to play favorites in New England, but I think, next to Rhode Island, Vermont just shot to the top of my list. There aren’t many places I visit where I feel like I don’t have enough time there. I’m usually always really ready to head home at the end of a trip, but Vermont is different. Driving along winding country roads, passing farms and covered bridges, it reminded me a bit of Ireland, a place that feels suspended in time. Forget strip malls, fast food and chain stores, what you’ll find in and around Woodstock is good old New England charm. Of course if you can get yourself there in the fall, you’ll be treated to one of the most spectacular shows of fall foliage, but I imagine no matter the season, there’s plenty to enjoy. Here’s some suggestions for what to pack, things to do, places to stay and most importantly where to eat!

Jess Ann Kirby wears a blanket scarf from Anthropologie for a cozy fall look in Vermont
Jess Ann Kirby looks out at the view of Mount Tom in Woodstock, Vermont
Jess Ann Kirby spends a weekend in Woodstock, Vermont in an Anthropologie cable knit sweater and blanket scarf

What to Pack

As with any New England destination, pretty much any time of year, my advice is always to bring layers. In the few days we were in Woodstock the temperature varied over 40 degrees (yes you read that correctly). Here’s what I brought with me.

Alternated between this blanket scarf and my travel wrap.
I love this quilted jacket from Anthropologie, so perfect for fall. Layered it over this embroidered blouse on warmer days.
These boots were my favorite the entire trip. They are SO comfortable. I also brought these ankle boots for walking around town.
This fisherman sweater is really cute. I wore it with these velvet skinny jeans.
For cozy lounging at our Airbnb I brought these sweatpants and this thermal (which was also great for layering under sweaters).
My trusty L.L. Bean fleece jacket.
I wore these skinny jeans most of the time.

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

Where to Stay

Our first visit to Woodstock we stayed at the Woodstock Inn which was really nice. They have incredible amenities, the most beautiful spa, and pet friendly rooms. If you want to stay at an inn/hotel I definitely recommend the Woodstock Inn. For our second trip we decided to rent an Airbnb, we usually prefer to do this when we travel as we get up early and like to be on our own schedule (book through this link and get $40 off your first Aribnb stay). We found the most spectacular cabin super close to town and it was absolutely perfect. The only downside is that it’s not pet friendly, but understandable as allowing pets inevitably means more wear and tear and this place is just pristine. Everything was brand new including the adorable kitchen with SMEG appliances. It sits overlooking a pond surrounded by trees. There’s also a cozy fireplace and lots of modern amenities. I can’t say enough good things about it, the owners were super responsive and accommodating, I would love to stay in this place in the winter!

Jess Ann Kirby stays at an Airbnb cabin during her visit to Woodstock, Vermont
Jess Ann Kirby shares her favorite places to stay, eat and shop in Woodstock, Vermont
Jess Ann Kirby shops at Farmhouse Pottery in Woodstock, Vermont for unique pieces to take home

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)

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
Mt Billings Farm
Go for a Drive – We hopped in the car and took a few scenic drives that were all 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

Jess Ann Kirby recommends shopping at the Vermont Flannel Factory during a visit to Woodstock
Jess Ann Kirby shares her top places to shop, eat and stay in Woodstock, Vermont
Jess Ann Kirby visits Barnard Silver Lake during a weekend getaway to Woodstock Vermont
Jess Ann Kirby recommends visiting Kelly Way Gardens when in Woodstock, Vermont

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). The chef is only 23!
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 – The sandwiches here are killer. 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.

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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