50 Things to Do in Litchfield County This Fall

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.

Drive route 7 to Kent
Route 44 to Falls Village
Lake Waramaug scenic route

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.

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.

5. Take a hayride.

6. Go pumpkin picking at a local farm.

7. Go to a fall festival.

18th Annual Connecticut Garlic & Harvest Festival on October 7-8
Washington Harvest Festival on October 10

New Milford Apple Festival8. Take a spooky walk through the Harrybrooke Park Haunted Trail in New Milford on October 13.

9. Celebrate at an Oktoberfest Festival.

Clocktown Cloctoberfest in Thomaston on October 8

3rd Annual Torrington Oktoberfest in Torrington on September 30

The Farm, Woodbury10. Paint pumpkins and have a glass of wine at Hawk Ridge Winery’s Forever Pumpkin Paint & Sip on October 12.

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 in Washington Depot

March Farm in Bethlehem

Averill Farm

13. Join the Bellamy-Ferriday House & Garden for Landmark Lunch and Learn! Hear stories they don’t tell you, the lesser known tales of Bellamy-Ferriday House & Garden.

14. Join Minor Memorial Library for a Halloween Storywalk on Joey’s Trail; learn about the Legend of Sleepy Hollow.

15. For some family fun and amazing Jack O Lantern carvings visit the Hollowed Harvest: Wicked Labyrinth in Plymouth from September 22 – October 31.

16. Take a cemetery tour.

All Hallows Eve at Glebe House Museum

Gunn Memorial Library & Museum’s Annual Cemetery Tour

A Tale of Two Cemeteries – A Lantern Tour of Downtown Terryville

17. Take your pup to Candlewoof Dog Park for their annual Howl ‘O’ Ween fundraiser on October 29. 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 36rd annual Columbus Day weekend arts & fine crafts show and restoration anniversary celebration. October 6-9, 13-15.

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 47th Annual Kent Pumpkin Run on October 29. Prizes will be given to the top five most creative costumes. Register here by October 27.

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:

Marty’s Cafe in Washington Depot

The Smithy Cafe in New Preston

Bridgewater Village Store in Bridgewater

River & Rail Cafe in New Milford

Toast & Co. in Litchfield

Arethusa a Mano in Bantam

Espresso 59 in Litchfield

The Po in Washington Depot

West Egg in Woodbury

Pumpkin Spice Latte22. 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 Roxbury25. Join the Litchfield Historical Society at the Tapping Reeve Meadow on October 14-31 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.

New Milford Farmers’ Market in New Milford
Litchfield Hills Farm-Fresh Market in Litchfield
Norfolk Farmers’ Market in Norfolk
The Morris Marketplace in Morris
Thomaston Farmers’ Market in Thomaston
Torrington Farmers’ Market in Torrington

29. Take a Pottery class

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

Housatonic Trading Co. in Bantam
Jeffrey Tillou Antiques in Litchfield
Elephant’s Trunk Flea in Market in New Milford
Privet House in New Preston
Mill House Antiques in Woodbury

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!

Charym in Litchfield
W. Rhythm Fitness in Kent
Litchfield Hills Fitness in Litchfield
EVOLVE Yoga Wellness Nutrition in New Milford

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.