Woodstock, VT Vacation Itinerary for Summer

How To Wear A Tunic Sweater
By Jess
7 Jun 2023

Let us take the guesswork out of your stay. If you’re in town for a few days or a long weekend, follow our recommended itinerary below for a fun-filled visit that shows you the best of Woodstock.

Included are a variety of activities that range from scenic hikes to biking adventures and spa treatments, along with some of my favorite places for retail therapy—hopefully a little something for everyone!

Keep in mind many restaurants also require reservations so please check their website and be sure to call ahead.

Our complete guide for your perfect 3-day trip to Woodstock during the summer season.

Woodstock, VT Vacation Itinerary for Summer

Travel & Lodging


Luxury/Cozy: Woodstock Inn

The Woodstock Inn and Resort is Woodstock’s most historic inn residing right in the village center. The Woodstock Inn makes your stay easy with all the amenities you need to enjoy a relaxing, quintessential Vermont vacation all in one location. Dine at the Red Rooster, relax at the spa, and lounge by the outdoor pool. You can also enjoy their off-site clubs including golf at the Woodstock Country Club and fitness classes and facilities at the Woodstock Athletic Club.

Family Friendly: 506 On The River Inn

506 On The River Inn is the perfect place to settle in for a Vermont vacation with the family. With everything from a bistro, pool, sauna, game room and kids playroom this makes for a great home base for families.

On A Budget: Sleep Woodstock

Located just a few minutes outside of the Woodstock village on route 4 heading west, Sleep Woodstock is a great budget motel. You can guarantee clean, updated rooms, comfortable beds and a quiet place to spend the night. While there aren’t any bells and whistles, Sleep Woodstock is a great place to base your travel while enjoying the town of Woodstock on a budget.





  • Take a walk through Middle Bridge to Faulkner Park and if you’re feeling ambitious walk up Mt. Tom (you can hike or take the access road through Billings Park).
  • Breakfast or a quick bite at Mon Vert. If you’re looking for something quick to grab and go all of their muffins and scones are delicious. If you’d like to sit down and enjoy the outdoor patio seating try their Breakfast Burrito or Challa French Toast. You can’t go wrong with their coffee and they always have fun new specials on each month to try!
  • Great weather Rent e-bikes from Woodstock Wheels and take a self-guided tour through one of the beautiful routes in Vermont.
  • Indoors Check out the Woodstock Athletic Club (they have a great indoor pool!)
  • Family friendly Check out Billings Farm and their educational exhibits, interactive programs and lots of animals.


  • Grab lunch at Village Butcher and bring it to eat at the picnic tables along the Ottauquechee River at East End Park
  • If you’re looking to dine in, check out Mon Vert for great salads and sandwiches. 


  • For a romantic and cozy dinner head to Prince and the Pauper. Reservations strongly recommended.
  • Casual/family friendly option: Get great burgers and farm to table pub food at Worthy Kitchen. In the summer there’s lots of outdoor seating. Reservations recommended.



  • Head to Silver Lake State Park in Barnard for swimming, paddling and exploring. You can pay for parking at the State Park which provides easy access to the sandy swimming area, lake, playground, restrooms, snack bar and more. There are paddle board and kayak rentals available too. It’s pet friendly in designated areas. 
  • On your way to Silver Lake get breakfast sandwiches to go at Village Butcher or stop by the Barnard General Store and order their delicious pancakes and egg sandwiches. They have lunch options too!


  • Dine at Simon Pearce Restaurant and enjoy delicious food with stunning views of the Ottaquechee River. After peruse through their flagship store and watch live glass blowing demonstrations.
  • Kid friendly option: Head to the White Cottage Snack Bar to order some yummy fried food, salads, seafood and ice cream. Take your food trays down to the river and set up camp at one of the picnic tables. Once your kids finish eating they can play in the shallow river.


  • Make a reservation for an exquisite farm to table experience at Sante right in the village.
  • White Cottage is great for kids at night too!



  • Early bird gets the best donuts! Head to The Butcher & Pantry in Brownsville for delicious crullers, coffee cake, cinnamon buns, coffee and more.
  • If you’re looking for a bigger sit down breakfast head to Mountain Creamery for a delicious no frills diner experience.
  • Head to Farmhouse Pottery and watch live pottery making while you shop their beautifully merchandised flagship store.


  • Head to Long Trail Brewery for great Vermont made beer and delicious pub style food along the Ottaquechee River.
  • Another great lunch option if you’re up for a short drive is Killington Distillery. Enjoy handcrafted Vermont spirits and farm to table food at the base of Killington mountain.


  • Make a reservation for a true farm to table experience at Cloudland Farm.
  • If you’re craving pizza, check out The Ransom Tavern at Kedron Valley Inn for delicious cocktails and wood-fired pizzas along with other delicious entree options, salads and apps.

Disclosure: if you buy something through the links on this blog, we may earn an affiliate commission. We only feature products we would personally recommend. Thank you for your support.

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