Things to Do in Woodstock, Vermont

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Need a postcard-perfect New England escape that blends timeless charm with natural beauty? Then let me tell you about Woodstock, Vermont. I’ve wandered through its covered bridges, sipped maple syrup on farmhouse porches, and taken in mountain views that made me pause and just breathe. This is one of those towns that feels both cozy and invigorating—whether you’re hiking in the hills or browsing handmade crafts around the village green. Woodstock is everything I love about Vermont wrapped into one idyllic spot.

Woodstock, VT Highlights:

For Adventurous Travelers: Hike to the summit of Mount Tom – I’ve done this trail more than once, and the views from the top never get old. You’ll climb through quiet forest paths in Marsh-Billings-Rockefeller Park and be rewarded with sweeping views over the valley—especially stunning in fall.
For History Buffs: Tour Billings Farm & Museum – I spent a half-day here learning how Vermont’s past was rooted in sustainable farming. You can meet the cows, see antique equipment, and explore exhibits that make local history feel vivid and real.
For Shoppers: Browse boutiques around the Village Green – This is one of my favorite downtown strolls. I’ve picked up artisan pottery, local honey, and a few too many books from the charming independent stores. It’s a great place to slow down and browse.
For Couples: Drive the scenic route through Quechee Gorge – If you’re here with someone special, this drive is a must. I’ve pulled over countless times for photos of the gorge and waterfalls, and the cozy cafés nearby make it perfect for a leisurely day together.
For Families: Visit Sugarbush Farm – I’ve brought family here for cheese tasting and maple syrup sampling (the real deal!). Kids love watching the sugaring process and walking the farm trails, and the views? Just wow.

Best Time to Visit Woodstock, VT

In my opinion, you can’t beat mid-September to October if you want to see fall foliage at its fiery peak. I’ve also visited in December when the town feels like a real-life snow globe—complete with wreaths on every door and twinkle lights in every window. Summer is ideal for hiking, swimming holes, and farmers markets, while winter brings snowshoe trails and nearby skiing, with fireside cocoa at cozy inns to cap the day.

How to Get to Woodstock, VT

By Car: I usually drive in via US-4—it's a scenic ride, especially in fall. Woodstock is about 30 minutes from White River Junction and a relaxed 2.5-hour drive from Boston.
By Train: Amtrak’s Vermonter line has a stop at White River Junction. I’ve taken it before and then hopped a quick taxi to Woodstock—it’s a nice, low-stress way to travel.
By Air: For short flights, I’ve used Lebanon Municipal Airport (LEB), just 25 minutes away. For bigger airports, Burlington (BTV) and Boston Logan (BOS) both work well if you don’t mind the scenic drive in.

Where to Stay in Woodstock, VT

Recommended for Families: 506 On the River Inn – I stayed here on a multigenerational trip, and it was a hit with everyone. The pool and playroom keep kids happy, and the riverside setting is peaceful and perfect for unwinding.
For Couples: Woodstock Inn & Resort – If you’re celebrating or just treating yourselves, this is the place. I’ve stayed here for a special occasion, and between the spa, the rooms, and the locally sourced food, it was unforgettable.
For Budget Travelers: Sleep Woodstock Motel – I’ve used this as a base for hiking weekends. It’s clean, quirky, affordable, and just outside town, with great access to the trails and parks I love most.