As the summer heat fades and the crisp autumn air settles in, Connecticut transforms into a haven of fall activities and scenic beauty. Whether you're a local looking for new adventures or a visitor eager to experience the best of New England, our list of 50 must-do activities this September will ensure you make the most of the season. From leaf-peeping to festival-hopping, here's your ultimate guide to fall fun in the Nutmeg State.

🍂 Outdoor Adventures

1. Hike foliage trails at Devil’s Den (Weston), Sleeping Giant (Hamden), or Devil’s Hopyard (East Haddam).

2. Go glamping at Hickory Ledges (Canton) or Getaway House (Moodus).

3. Kayak or paddleboard on the Saugatuck River (Westport) or Candlewood Lake (Danbury).

4. Take a thrilling zipline ride at The Adventure Park (Bridgeport).

5. Try axe throwing at Stumpy’s Hatchet House (Fairfield).

6. Bike the Norwalk River Valley Trail or the Air Line State Park Trail.

7. Sail Long Island Sound from Norwalk or Stamford.

8. Ride horses at Silvermine Equestrian (Norwalk).

9. See Connecticut’s fall colors from the sky on a hot air balloon ride in Plainville.

10. Explore covered bridges in Cornwall or Kent.

11. Ride the Essex Steam Train for classic foliage views.

🍎 Fall Traditions

12. Pick apples and pears at Silverman’s Farm (Easton) or Lyman Orchards (Middlefield).

13. Visit Beardsley Zoo (Bridgeport) or the Connecticut Audubon (Fairfield).

14. Leaf-peep along scenic Route 7 through the Litchfield Hills.

15. Take a guided history walking tour in Fairfield, Ridgefield, or Mystic.

16. Join a ghost tour in New Haven, Norwich, or at the Fairfield Museum.

🎭🏈 Entertainment, Culture & Sports

17. Cheer on the Huskies at a UConn football game in East Hartford.

18. Catch a performance at the Westport Playhouse or ACT of CT (Ridgefield).

19. See a drive-in movie in Southington or at the Mansfield Drive-In.

20. Stroll the Sculpture Grounds in Old Lyme.

21. Follow the Connecticut Art Trail — highlights include the Aldrich Contemporary Art Museum (Ridgefield) and MoCA Westport.

🎉 Festivals & Seasonal Events

22. Feast at the Norwalk Oyster Festival (Sept 6–8).

23. Step back in time at the Connecticut Renaissance Faire in Lebanon (weekends).

24. Celebrate nautical heritage at the Maritime Festival in Mystic (Sept 14–15).

25. Enjoy harvest festivals at Silverman’s Farm (Easton) and Jones Family Farms (Shelton).

26. Get lost in a pumpkin patch or corn maze at Plasko’s Farm (Trumbull) or Bishop’s Orchards (Guilford).

27. Get spooked at haunted attractions like Legends of Fear (Shelton) or Fright Haven (Stratford).

28. Shop artisan goods at craft fairs in Guilford or Stamford’s Harbor Point.

🛶 Cozy Escapes

29. Stay at the Inn at GrayBarns (Norwalk) or The Homestead (Madison).

30. Wander charming towns like New Canaan, Essex, or Litchfield.

31. See autumn blooms at Bartlett Arboretum (Stamford).

32. Antique in Woodbury or Stamford.

33. Treat yourself to a spa day at Delamar Southport or Saybrook Point Resort.

34. Sip sunset cocktails at Sign of the Whale (Stamford).

35. Take a sunset cruise from Norwalk or Mystic.

36. Gather with friends by bonfires at Sherwood Island State Park (Westport).

🍽 Food & Drink

37. Indulge in BBQ at Hoodoo Brown (Ridgefield) or Bobby Q’s (Norwalk).

38. Savor a last lobster roll of the season at Rowayton Seafood, Southport Deli, or Abbott’s (Noank).

39. Enjoy fall ice cream at Ferris Acres Creamery (Newtown) or Saugatuck Sweets (Westport).

40. Dine outdoors at waterfront spots like L’Escale (Greenwich) or The Whelk (Westport).

41. Sip wine at Jones Winery (Shelton) or Hopkins Vineyard (New Preston).

42. Try local brews at Two Roads Brewing (Stratford).

43. Join a walking food tour in New Haven or Mystic.

44. Shop seasonal produce at farmers’ markets in Fairfield, Westport, Wilton, or Greenwich.

🌟 Unique Experiences

45. Discover charming small towns like Essex, Kent, or Ridgefield.

46. Visit botanical gardens with fall blooms at Elizabeth Park (West Hartford).

47. Wander the Sculpture Mile in Madison.

48. Go antiquing in Connecticut’s “Antiques Capital” — Woodbury.

49. Watch wildlife at sanctuaries like Sharon Audubon Center.

50. Experience a cozy evening by an outdoor bonfire with friends at local parks.

September in Connecticut offers a perfect blend of summer's last hurrah and fall's first embrace. From outdoor adventures and cultural experiences to food festivals and scenic drives, there's something for everyone to enjoy. So grab your flannel shirt, put on your hiking boots, and get ready to create unforgettable memories this fall in the beautiful Nutmeg State.

Remember to check event dates and make reservations where necessary, as some activities may have limited availability. Happy exploring!

Last updated: August 2025