32 Things to Do in Connecticut This September Last Updated 10/19

Looking for something to do in Connecticut in September? Whether you want something active or relaxing, cultural or nature-oriented, historic or trendy, there is always so much to do, and it’s all so close together. Here are some highlights for September.

For even more ideas check out CTvisit.com where you can search by type of activity under the “DO” navigation tab, or browse articles full of ideas under the “IDEAS” tab.

Active Adventure

1. Take a scenic hike. Catch a glimpse of the first signs of fall foliage on one of Connecticut’s many hiking trails.

2. Glamp under the stars. Ditch the hustle and bustle of the city for a rustic retreat at Tamarack Lodge in Voluntown.

3. Get out on the water. Experience nature’s beauty by kayak or paddleboard on Black Hall Outfitters’ Eco-Paddle Tour or Sunset Paddle Tour in Old Lyme.

4. Soar through the trees. Get a birds-eye view of the leaves beginning to change during zipline tours at the Adventure Park at the Discovery Museum in Bridgeport or HighFlyer Zipline at Foxwoods in Mashantucket.

5. Pedal around. Grab a bike and get out on any of Connecticut’s biking trails to take in the early signs of fall or plan your own scenic biking trip to see a few of the state’s covered bridges.

6. Experience the tree swallow migration. Hundreds of thousands of tree swallows gather on the Connecticut River every year—observe them on a RiverQuest or Becky Thatcher Riverboat cruise.


Arts, Culture & Sports

7. Live like a Gilmore Girl. Plan a quick getaway to explore the towns that inspired the hit television show, topping it off with the 2019 Fan Fest at the end of the month.

8. Enjoy art, outdoors. While the weather is still warmer, plan a visit to any of the state’s sculpture gardens including Studio 80 + Sculpture Grounds in Old Lyme or Garden of Ideas in Ridgefield. Don’t miss the Newtown Arts Festival.

9. Tailgate at a football game. School is back in session, and so is football! Relax with some friends as you wait for a big Yale or UConn game to start.


Food and Drink Adventures

10. Go on a foodie tour. Follow the pizza, chocolate, or chowder trails or book a Taste of New Haven Tour.

11. Grab one more lobster roll. Before Connecticut’s seafood shacks close for the season, grab one more hot buttery lobster roll to last you through next spring and don’t miss the 49th Annual Chester Lobster Festival.

12. Sample hard cider. Plan a visit to one of Connecticut’s hard cider destinations including the newest cider tap room, Yankee Cider Barn at Staehly Farms.

13. Dine outside. Before it gets too cold, take all the opportunities you can get to enjoy outdoor dining at any of these restaurants around the state.

14. Sip new brews. Indulge in all kinds of flavors and styles at any of the fall beer festivals happening around the state.


Family Fun

15. Go apple picking. Connecticut is filled with locally-owned farms and orchards that let you fill up your baskets with fresh apples and other baked goods.

16. See some wild animals. Come face to face with zebras, elk, bison and more at the Action Wildlife Foundation in Goshen or Connecticut's Beardsley Zoo in Bridgeport.

17. Attend a Country Fair. From midways to music, livestock competitions to deep-fried everything, there’s no better way to spend a day, night or weekend than at one of the state’s Country Fairs. The Durham Fair is celebrating 100 years!

18. Get Lost in a corn maze. Test your skills at one of the fun and challenging corn mazes around the state including Lyman Orchard’s NASCAR-themed maze in Middlefield.

19. Visit the Mayflower II. Celebrate the official launch and re-commissioning of Mayflower II at Mystic Seaport Museum before it set sails in Spring 2020.

20. Celebrate Connecticut Day at The Big E. See all that Connecticut has to offer on Wednesday, September 18, at The Big E—including live performances, special activities and more. Learn more here

21. Travel back in time. Experience the enchanted recreation of a 16th-century harvest festival at the 21st Annual Connecticut Renaissance Faire, or check out vintage airplanes and cars at the 33rd Annual Simsbury Fly-In, Car Show & Food Truck Festival.



22. Treat yourself to the spa. Visit any of Connecticut’s spas for a fall treatment to help ease your way into the new season.

23. Stay in a B&B. West Lane Inn in Ridgefield, Stonecroft Country Inn in Ledyard, Connecticut River Valley Inn in Glastonbury and Homestead Inn in Greenwich offer hospitality so warm it’ll keep you cozy as the temperature drops.

24. Find some small-town charm. Stroll, shop, or dine in one of the state’s picturesque towns.

25. Go for a scenic train ride. Take in Connecticut’s beautiful scenery by train including the Railroad Museum of New England’s Fall Chocolate Decadence Tour or aboard the Essex Steam Train.

26. Stroll through a few fall gardens. Stop and smell the flowers and watch the natural colors of fall take over at some of Connecticut’s great fall garden destinations.

27. Reel in some trout. Trout is one of Connecticut’s most sought-after freshwater game fish and September is a great time to plan a fishing trip on the Salmon, Farmington or Housatonic rivers.

28. Go antique shopping. Look for hidden treasures by planning an outing on Connecticut’s antique trail.


Romantic Escapes

29. Plan a romantic weekend. As crowds disperse, plan a last-minute getaway to one of Connecticut’s romantic inns by the sea.

30. Cozy up by the fire. Enjoy a delicious fireside meal and cozy atmosphere at any of Connecticut’s restaurants with fireside dining

31. Go for a cruise. Before temperatures drop too much, set sail on the historic Argia in Mystic or Onrust in Essex; or, book a sunset cruise on the R/V Spirit of the Sound from Maritime Aquarium in Norwalk.

32. Follow the wine trail. If you haven’t already, grab your passport to Connecticut Farm Wineries and take in the scenic views at any of these Instagrammable vineyards and wineries. Or, test your skills at the Grown Up Corn Maze Adventure at Holmberg Orchards & Winery in Gales Ferry.