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!
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.
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!
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.
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
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.