The 56th annual New Canaan Nature Center Fall Fair opens Friday, October 9. One week later, the New Canaan Museum & Historical Society holds a Historic House Tour to mark the semiquincentennial. The two events sit on the same road. The fair is at 144 Oenoke Ridge and the tour starts from the Museum at 13 Oenoke Ridge. Between October 9 and 18, the town's America250 calendar lists only those two events. The Fall Fair appears once. The Museum's October 17 tour appears twice, as the Historic House Tour and as the New Canaan Historical and Colonial Home Tour, and the second listing describes the Museum's first-ever tour of the town's oldest homes. Its one other nearby entry is a Ken Burns American Revolution screening on Thursday, October 8.
So New Canaan's 250th year doesn't come with a big new festival this October. It runs through an old fair and some old houses. Add the Carriage Barn Arts Center's fourth Waveny Arts Festival on Sunday the 11th and a full week of smaller evening programs, and most of the town's fall calendar fits into ten days. The hours, parking and ticket rules below are what decide how much of it fits into one family's weekend.
The First Weekend, Day by Day
Friday, October 9: The Fair's Ticket Rules Change at Night
The Fall Fair runs Friday 5 to 9 p.m., Saturday 10 a.m. to 6 p.m. and Sunday noon to 5 p.m. Friday night works differently from the rest of the weekend. Fair tickets cost $1 each, and a $35 wristband covers unlimited carnival rides, but only on Friday night. On Saturday and Sunday you pay ride by ride. A child who rides a lot gets the most out of the wristband on Friday evening. A child who wants two rides and some time with the goats will spend less on Saturday.
The fair's CTvisit listing describes carnival rides, children's games, a zipline, pumpkin decorating and Nigerian Dwarf goats. The fair's campaign page says food, drinks and snacks will be available to purchase. The wristband campaign says there is no on-site parking at the Nature Center. No shuttle or off-site parking details had been posted when this was written, so check the Fall Fair page before you go, especially if you're thinking of driving over at Friday rush hour.
Earlier that day, New Canaan Library hosts a talk on healthy aging with Staying Put, from 10 to 11 a.m. in the Library's Tate Conference Room.
Saturday, October 10: A Garden Hour Before the Fair Fills Up
Grace Farms holds its Autumn Stroll on Saturday from 11 a.m. to noon. The Grace Farms Garden Team leads the walk. On the same day, the Grace Farms events calendar lists Open Arts Studio from 10 a.m. to 2 p.m. and Imagination Playground from 10 a.m. to 5 p.m. Saturday is also the fair's longest day, 10 a.m. to 6 p.m., so a family can walk the grounds at Grace Farms in the morning and still have most of the afternoon on Oenoke Ridge.
Sunday, October 11: Two Events, Four Shared Hours
Sunday is the day that takes the most planning. The arts festival opens two hours before the fair, and the fair stays open an hour after the festival closes.
| Time | Waveny Arts Festival, Waveny Park | Fall Fair, 144 Oenoke Ridge |
|---|---|---|
| 10 a.m. | Opens, free | Closed |
| Noon | Open | Opens |
| 4 p.m. | Closes | Open |
| 5 p.m. | Closed | Closes |
A morning at Waveny and an afternoon at the fair covers both without overlap. The festival is free, and the Carriage Barn Arts Center presents it. The lineup includes fine art photographers, jewelry designers, painters working in everything from abstract to landscape, mixed media, three-dimensional work, block-printed textiles, ceramics, hand-poured candles, clothing, stationery and ornaments. The organizers say most of the artists, performers and food vendors come from New Canaan and nearby towns.
The program is listed by name. The Parkway Ramblers play bluegrass, New Canaan Town Brass performs, and the Connecticut Stage Company previews its "My Fair Lady." This year adds dance from the New England Academy of Dance and its professional company, Thomas Ortiz Dance. Food comes from Mobile Pie, Taco Tequila, Farmer's Grind Coffee, So Fresh Doughnuts and the South Norwalk Ice Cream Truck. A Young Entrepreneurs Marketplace returns with 30 kids and teens, ages 9 to 17, showing their own businesses.
That "My Fair Lady" preview links the two weekends. The full production opens the following Saturday.
The Week Between
The weekdays are quieter but not empty. Several of the evening programs pick up the Halloween season early.
- Thursday, October 15, 7 to 8 p.m. New Canaan Library hosts "Toil and Trouble: The Supernatural in the Plays of Shakespeare," a free performance-lecture.
- Thursday, October 15, 7 to 9 p.m. The Nature Center's fall candle-making workshop costs $105. Participants make a candle, a sugar scrub and a rollerball fragrance.
- Friday, October 16, 6:30 to 10:30 p.m. ABC New Canaan's Oktoberfest takes place at the Carriage Barn, as currently listed in New Canaanite's local roundup.
- Tuesday, October 20, noon to 1 p.m. The New Canaan Museum & Historical Society holds a Lunch & Learn with Dr. Scott Moore on the history of witch trials in Connecticut and Virginia.
Thursday the 15th has two programs at the same hour. The Library talk is free and lasts an hour. The candle workshop is paid, runs two hours and probably needs advance sign-up, so it calls for the earlier decision.
Saturday, October 17: Back to Oenoke Ridge
The Historic House Tour runs from 1 to 5 p.m. and costs $165. It honors America's semiquincentennial with visits to landmark buildings: private residences, a restored chapel and what the Museum calls a majestic barn. Guests ride between stops in small vans, and an architect docent leads the tour at each one. The tour features the town's Colonial homes in particular. Those houses usually turn up as backdrops on a drive along the ridges, and the tour lets you go inside them with someone who can explain how they were built.
The rest of that Saturday fills in around the tour:
- Grace Farms, Tea Diplomacy. Grace Farms lists this as a featured program for Saturday, October 17.
- Connecticut Stage Company, "My Fair Lady." The opening-night party runs 5:30 to 6:30 p.m. and the performance 7 to 10 p.m. A second listed performance is Sunday, October 18, at 2 p.m.
The house tour ends at 5 p.m. and the opening party starts at 5:30. Anyone booking both will have a short gap between them.
Dates Past the Tenth Day
Several later fall dates take a ticket, a reservation or at least a spot on the calendar now.
- October 22. The Glass House holds its second Golden Hour Tour of the fall. The first is October 8. The 2026 tour season ends December 14. Silvermine's 76th A•ONE exhibition closes the same day.
- October 24. Grace Farms hosts an architecture talk with its founders.
- October 30, 5:30 to 7:30 p.m. The Nature Center's Halloween Spooktacular includes animal encounters, crafts, a campfire and a jack-o'-lantern walk. Admission is $15 per person, and children 2 and under are free.
- November 3, 11 a.m. to 1:30 p.m. The Museum's Election Day program opens its buildings and offers a patriotic craft, a children's vote, trucks and a bounce house.
- November 7 and 8. Silvermine's Artisans Market brings together 20-plus makers working in textiles, jewelry, wood, glass, paper and ceramics. The Holiday Salon, The Gift of Art, opens November 7 and runs through December 23.
- November 15. Nemanja Radulović and Double Sens perform at Grace Farms.
- November 21, 10 a.m. to 5 p.m. The Nature Center's free Holiday Market features artisan gifts and a School of Rock performance.
The Nature Center opens the stretch with the Fall Fair and closes it with the Holiday Market six weeks later. Between them, the Museum carries most of the semiquincentennial programming from its building a few addresses up Oenoke Ridge.
If you're hosting family for one of these weekends, or you'd like ideas for out-of-town guests who want to see the Colonial houses on the tour, Rachel Walsh is happy to help with suggestions, from the Waveny Arts Festival to a Golden Hour slot at the Glass House. Book an Appointment and we can plan it together.