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50 Things to Do in Litchfield County This Fall
Allie Steers

50 Things to Do in Litchfield County This Fall

August 22, 2025

By Allie Steers, Elizabeth Deegan, and Zandria Oliver

Fall is here, and the exquisite fall foliage, crisp weather, and fall activities make Litchfield County exceptionally magical this time of year. Check out our list of festive fall activities, from gorgeous leaf-peeping spots, to fall festivals, pumpkin patches, corn mazes and more.

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. Take a hayride.

6. Go pumpkin picking at a local farm.

7. Go to a fall festival.

8. Take a spooky walk through the Harrybrooke Park Haunted Trail in New Milford on Fridays & Saturdays starting October 11.

9.  Celebrate at an Oktoberfest Festival.

 

10. Create a spooky wreath and have a glass of wine at Hawk Ridge Winery’s Halloween Wreath Making on October 2.

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.

 

13. Take a trip to the Harwinton Fair, running  October 3-5.

14.  For all the foodies out there, attend Litchfield Magazine’s Savor Litchfield on September 14 at South Farms. Buy tickets!

15.  Attend the Warner Theatre’s Annual Wine and Food Tasting on October 25. Buy tickets here!

16. Take a cemetery tour.

17. Have a scenic picnic, walk or a beautiful photo op at Topsmead State Forest.

18. Pop into the Merwinsville Hotel’s 38th annual Columbus Day weekend arts & fine crafts show and restoration anniversary celebration. October 10-13 and 17-19.

19. Check out Trunk or Treat in New Milford on October 26 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 49th Annual Kent Pumpkin Run on October 26. Prizes will be given to the top five most creative costumes.

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:

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 18 – November 2 for Scarecrows in the Meadow.

26. Bookstore tour, to prepare for colder days-in reading a book by the fireplace or for inspiration to join a book club.

27. Visit the elephant’s trunk flea market.

28. Explore local Farmer’s markets while they’re still open – perfect for finding hot cider and local produce and goods. Here are just a few of the many markets.

29. Take a Pottery class.

30. Go antiquing, here are a few antique stores to stop in!

31. Go see a movie at an outdoor/drive-in movie theater

Four Brothers Drive Inn in Amenia

The Judy Black Memorial Park and Gardens in Washington

32. Get relaxed or back in shape with yoga / fitness classes in the area. Here are a few of many fitness / yoga studios in the county!

33. Kayak and fish in Bantam Lake, the largest natural lake in Connecticut covering 947 acres. There are two launches, Beverly’s Marina at the corner of Rt. 209 and Palmer Road in Morris, or White Memorial Family Campground Launch.

34. Take a cooking class to show off your new recipes and skills during the holiday season

35. Spend the day at a beautiful vineyard. Litchfield County has numerous vineyards to enjoy. Bring a picnic blanket and some chairs and relax while sipping on wine and watching the sunset. Check their websites for special live entertainment events. Here are just a few: Hopkins Vineyard in Warren; Spring Hill Vineyards in New Preston; Hawk Ridge Winery in Watertown; Connecticut Valley Winery in New Hartford; Sunset Meadows Vineyards in Goshen.

36. Go brewery/distillery hopping! Here are just a few:

37. Visit local cidery, Park Lane Cider Mill in New Milford for some freshly pressed cider.

38. Visit an animal sanctuary, bird sanctuary, or farm!

39. Take an art class!

40. Go see some live music

41. Go see a play or show at a local theater.

42. Try out Horseback riding!

43. Try curling at Norfolk Curling Club in Norfolk.

44. Have some family fun and go bowling

45. A thrifting excursion to revamp your wardrobe more sustainably

46. Get primped with a new hairstyle or nails at local salons, or even have a spa day! Here are a few places:

47. For history buffs, visit the litchfield history museum

48. Admire the beautiful waterfalls of Litchfield County. Do go chasing waterfalls.

49. Art gallery tour

50.  Visit Great Acres Farm in Goshen for their yearly haunted house; the Forsaken Lands running September 27-November 1.

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