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Overlooking vermont scenery

From The Blog September in Woodstock

Embrace the early whispers of fall Discover Woodstock in September

September is a magical time when the first hints of fall colors begin to paint the landscape. Dive into the rich tapestry of autumnal activities, savor the harvest season, and immerse yourself in the cultural festivities that define America’s most beautiful village.

Hiking Mt. Tom
Group of men fly fishing


September's mild temperatures and crisp air make it a prime month to explore the great outdoors of Woodstock. As the leaves begin their transformation, the town and its surroundings offer a kaleidoscope of colors that are a feast for the eyes.

  • For those who love hiking, the trails of Mt. Tom offer a panoramic view of the changing foliage. The vibrant reds, oranges, and yellows are a sight to behold from the mountain's peak. The water activities are equally breathtaking! Consider a serene canoe on nearby Silver Lake and be mesmerized by the reflections of fall colors!
  • If you’ve been waiting to dip your toes into the incredible sport of Fly Fishing, now is your chance! Join the Woodstock Inn & Resort Orvis Endorsed Guide Team in a fly fishing course or check out their services including trip guiding and events. 
  • Stop by the Billings Farm National Park Forest Festival for some (free) family fun! Take a horse-drawn wagon ride, try your hand at woodworking, or explore the forest on a guided nature walk. Witness the whole forest product cycle in action, from horse-logging, to board cutting with a portable sawmill to woodcraft demonstrations. 
TEDx Event


September continues to celebrate the rich artistic heritage of Woodstock. As the season changes, so does the flavor of the arts.

  • Join Woodstock the weekend following Labor Day weekend to celebrate local artists at The Woodstock Art Festival. Enjoy a weekend-long event of fine art, music, spirits, and food, sponsored by the Woodstock Area Chamber of Commerce. Over 30 New England artists offer landscapes, portraits, photography, and more!
  • Experience Woodstock’s newest banner event: TedX Hartland Hill. This year’s theme, The Art of Living, explores balance and purpose in our lives and will feature a diverse lineup of world-class speakers. As with any TED event, prepare for an intellectual conversation that stimulates new perspectives, and leaves you inspired.
Farm stand
Cheese board
Red Barn Dinner Series

Savor the Season’s Bounty

September is a time of abundance in Woodstock. The harvest season brings fresh fall produce, making this time of year a savory delight for visitors and locals alike. If you happen to join us for a mid-week stay, enjoy the Farmers Market on the green! Here, local vendors offer the freshest baked goods, produce, and snacks, to the tune of live music each Wednesday afternoon.

  • Of course, Apple picking is a favorite pastime in September. Visit any of the local orchards and fill your basket with a variety of delicious apples. Don't forget to try the freshly made apple cider and pies – or a savory Apple Cider donut with your morning coffee at Mont Vert Cafe!
  • Looking to try some of the fresh local harvest straight from the source? Visit Woodstock’s local farm stands for late summer tomatoes to the first squash of the season.
  • Taste season flavors and mingle with the locals at one of the many local Farmers’ Markets around Woodstock. Shop farmed and foraged goods and local crafts. During peak foliage, we recommend Mt. Tom Farmers Market in South Pomfret. This is Woodstock’s oldest open air market and the perfect spot to shop surrounded by foliage views in every direction.
  • More interested in the dairy harvest? Sample the salty, nutty, and sharp cheddar cheese Vermont is known for by visiting the 8 local cheese makers around Woodstock. A perfect way to see the local landscape and visit local farms all in one trip.
  • For those looking for a more culinary farm-to-table experience, we recommend the Red Barn Dinner Series. Enjoy an intimate dining experience including cocktails in the Kelly Way Gardens and a seasonal menu handcrafted specifically for your meal. Make sure to reserve in advance!
girls and pumpkins