Litchfield County: Happening in the Hills
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Allie Steers

25 Things to Do in Litchfield County This Fall

By Allie Steers

Fall is here, and the exquisite fall foliage, crisp weather, and fall activities make Litchfield County exceptionally magical this time of year. If you’re yearning for some festive fall activities, we’ve got you covered, from gorgeous leaf-peeping spots to fall festivals and locals cafes with hot drinks. Check out our list for inspiration this fall. 

1. Go leaf peeping.

2. Take a scenic hike at one of the many preserves and parks around us. Each offers varying levels of trails and points of interest.

3. Get lost in a corn maze.

Bunnell Farm Corn Maze

4. Take a guided e-bike tour with Covered Bridge Electric Bike in West Cornwall or KC&E Adventures and experience the bucolic views that Litchfield County has to offer.

E-bike
KC&E Adventures

5. What better way to embrace fall than by cozying up under a big blanket? Knit a chunky blanket with Reis Learning Center on October 9. Register here.

6. Go pumpkin picking at a local farm.

Angevine Farm

7. Go to a fall festival.

New Milford Apple Festival

8. Take a spooky walk through the Harrybrooke Park Haunted Trail in New Milford on October 15.

9.  Celebrate at an Oktoberfest Festival.

The Farm, Woodbury

10. Paint pumpkins and have a glass of wine at Hawk Ridge Winery’s Faux Pumpkin Paint & Sip on October 15 or 20.

11. Visit the Railroad Museum of New England in Thomaston and take one of their Autumn Colors Limited train rides to see the fall foliage in Litchfield County.

12. Go apple picking at a local farm.

Averill Farm

13. Join the Bellamy-Ferriday House & Garden, the Bethlehem Land Trust, and the Old Bethlem Historical Society for a guided Fall Foliage Walk on October 9! Explore the historic grounds of the Bellamy-Ferriday House & Garden, the Bellamy-Ferriday Preserve, and the Old Bethlem Burial Grounds and learn the history of these places that once made up a working farm. Register here.

14. Join author and historian Peter Vermilyea for Witches in Connecticut as he discusses the lives of four 18th century residents of Litchfield County who were accused of witchcraft, their alleged activities and the possible motivations behind the accusations.

15. Go to the Hollowed Harvest Jack-O’-Lantern Festival in Plymouth which features dozens of large Jack-O’-Lantern displays. Great for all ages. Register here.

16. Take a cemetery tour.

17. Take your pup to Candlewoof Dog Park for their annual Howl ‘O’ Ween fundraiser on October 30. There will be raffles, a dog costume contest, New Milford Police K-9 demonstration, giveaways, photo booth, and more. 

18. Pop into the Merwinsville Hotel’s 33rd annual Columbus Day weekend arts & fine crafts show and restoration anniversary celebration. October 9 – 11, October 15 – 17.

19. Check out Trunk or Treat in New Milford on Halloween night and experience the Thriller Flash Mob in the middle of the green.

20. Run or walk in Kent’s largest one-day community event, the 45th Annual Kent Pumpkin Run on October 31. Prizes will be given to the top five most creative costumes. Register here by October 29.

21. Nothing screams fall quite like sipping on a hot drink from a local cafe. We are lucky to have so many around us. Here are just a few offering delectable eats and drinks that will warm you up:

Pumpkin Spice Latte

22. Check out Edward Tufte’s Landscape Sculpture Farm, Hogpen Hill Farms, with five miles of walking trails. Register here.

23. Do the Wigwam Escape room at The Institute for American Indian Studies and learn a new way to interact with history.

24. Visit a local farm stand and pick up some fresh produce while getting in the fall spirit! They are decorated for the fall season and have many fresh produce items!

Maple Bank Farm in Roxbury

25. Join the Litchfield Historical Society at the Tapping Reeve Meadow on October 29 for Stories to Keep You Up at Night, a special spooky night of Litchfield’s most scary stories! Register here

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