is still plenty to enjoy this fall in Westport, Weston and the surrounding Connecticut towns. Upcoming highlights include the Westport Farmers Market on Thursdays through November 5, Spirits of 1776 at Lachat Town Farm on October 22–25, theatrical ghost tours in Norwalk on October 22–24, and a new production at Westport Country Playhouse beginning October 20.
Whether you already live here or are exploring a move to Fairfield County, these outings offer a wonderful way to experience the community beyond its homes and neighborhoods.
Upcoming Fall Events at a Glance
Event | Town | Upcoming dates |
|---|---|---|
Westport Farmers Market | Westport | October 15, 22 and 29; November 5 |
Pride and Prejudice, Part 2: Napoleon at Pemberley | Westport | October 20–November 7 |
Spirits of 1776 | Weston | October 22–25 |
Ghosts & Spirits at the Mansion | Norwalk | October 22–24 |
Legends of Fear | Shelton | October 16, 17, 18, 23, 24, 25, 29 and 30; November 1 |
Schedules and ticket availability can change. Use the organizer links below to confirm your plans before visiting.
Westport Farmers Market: A Thursday Autumn Tradition
Upcoming dates: October 15, 22 and 29, and November 5, 2026
Hours: 10 a.m.–2 p.m.
Location: 50 Imperial Avenue, Westport, CT
The Westport Farmers Market makes a lovely starting point for a fall day close to home. Browse the market, pick up ingredients for a seasonal meal, and build in time to enjoy Westport afterward.
For someone considering living in Westport, visiting a local market can also give you a feel for everyday life: the places people gather, the businesses they support, and the routines that make a town feel familiar.
Visit the Westport Farmers Market website.
Spirits of 1776 at Lachat Town Farm in Weston
Dates: October 22–25, 2026
Location: 106 Godfrey Road West, Weston, CT
Admission: $25 per person
Recommended ages: 12 and older; children under 16 must be accompanied by an adult
Lachat Town Farm’s Spirits of 1776 combines Revolutionary-era storytelling with an immersive Halloween walking experience. Live performers and unexpected encounters bring the farm’s wooded setting into the story during an approximately 45-minute guided tour.
Tours begin at 6:30 p.m., with additional departures every 20 minutes. Reserve a timed ticket and dress for the weather and varied terrain. The production includes intense scenes, loud sounds and strobe effects, so consider each visitor’s comfort with frightening experiences.
This is a distinctive option for older children, teens and adults looking for a Halloween outing in Weston.
See details and reserve Spirits of 1776 tickets.
Ghosts & Spirits at Lockwood-Mathews Mansion in Norwalk
Dates: October 22–24, 2026
Tour departures: Every 20 minutes from 6 p.m. through 8:40 p.m.
Recommended ages: Adults and children 12 and older; children must be accompanied by an adult
For a Halloween evening with an architectural and historical setting, consider Ghosts & Spirits at the Lockwood-Mathews Mansion Museum.
These theatrical tours explore Victorian Spiritualism, Gothic literature and stories associated with the mansion. Visitors move through its rooms as performers weave together history and the supernatural.
It is an appealing choice for those who enjoy atmospheric storytelling in a historic setting.
View the museum’s event details and ticket link.
Live Theater at Westport Country Playhouse
Production: Ken Ludwig’s Pride and Prejudice, Part 2: Napoleon at Pemberley
Dates: October 20–November 7, 2026
Location: 25 Powers Court, Westport, CT
A fall evening at Westport Country Playhouse offers another way to enjoy the season. This world-premiere production imagines life after Elizabeth Bennet marries Mr. Darcy, with an unexpected arrival at Pemberley: Napoleon Bonaparte.
Choose a performance, plan dinner beforehand, and enjoy an evening centered on one of Westport’s cultural institutions. It is a particularly good option for a date night or a visit with friends who prefer theater to Halloween attractions.
Explore the Playhouse’s upcoming performances.
Legends of Fear: A Halloween Outing in Shelton
Location: 2 Saw Mill City Road, Shelton, CT
For those willing to venture beyond the Westport–Weston area, Legends of Fear offers a haunted hayride and The Hallow walking trail.
The remaining published 2026 schedule includes:
- Hayride and walking trail: October 16, 17, 23, 24, 25 and 30, and November 1.
- Walking trail only: October 18 and 29.
Select the date and attraction combination that suits your group. This is a more intense Halloween experience, so review the organizer’s visitor information before purchasing tickets.
Check Legends of Fear’s operating calendar and tickets.
My Insider Perspective: Experience the Town Before Choosing a Home
Having lived in Connecticut most of my life, I know how much the smaller details matter when choosing where to live. A farmers market, a community farm and a local theater reveal different aspects of a town’s character.
If you are considering a move, make time to explore beyond the properties on your tour. Spend a Thursday in Westport, attend an evening event in Weston, or explore Norwalk’s cultural offerings. Notice which setting feels comfortable and which activities you would enjoy returning to.
You can begin with my Fairfield County neighborhood guides and home-buying information.
Frequently Asked Questions About Fall Events in Fairfield County
What fall events are still happening near Westport after October 12, 2026?
Upcoming options include the Westport Farmers Market, Spirits of 1776 in Weston, Ghosts & Spirits at Lockwood-Mathews Mansion in Norwalk, performances at Westport Country Playhouse, and selected nights at Legends of Fear in Shelton.
When is Spirits of 1776 at Lachat Town Farm?
Spirits of 1776 takes place October 22–25, 2026, at Lachat Town Farm in Weston. The organizer recommends it for ages 12 and older.
Is the Westport Farmers Market still open in the fall?
Yes. Its published outdoor schedule continues on Thursdays from 10 a.m. to 2 p.m. through November 5, 2026, at 50 Imperial Avenue.
Which outings suit visitors who prefer a quieter fall experience?
The Westport Farmers Market and a performance at Westport Country Playhouse are good alternatives for visitors who prefer shopping, food and theater to haunted attractions.
Marketing & Local Expertise
I’m Christine Finch Oleynick, a REALTOR® with Keller Williams Gold Coast and a frequent real estate expert on News 12 Connecticut. My background includes more than 20 years in advertising, marketing and media, informing how I advise clients and present homes.
For buyers, local knowledge helps connect a home search with the way you want to live. For sellers, thoughtful preparation, pricing, photography, video and digital exposure help communicate both a property’s features and its setting.
If a move is on your horizon, explore my selling resources or reach out for a conversation about your plans.
Final Thoughts
Fall in Fairfield County still has much to offer, from an autumn market morning to theater and Halloween storytelling. Choose an outing that suits your interests and enjoy getting to know the places that make this area special.
For my full Fall Guide to Westport, Weston and the surrounding towns, email me with “FALL” in the subject line. If you are thinking about buying, selling or relocating, I would be happy to help you explore your options.
Christine Finch Oleynick, REALTOR®
Keller Williams Gold Coast | Luxury Real Estate Advisor
Email: [email protected]
Phone: 203-912-9712
Website: christinefincholeynick.com
Instagram: @christine_finch_oleynick
YouTube: Moving to Fairfield County CT
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Author Bio
Christine Finch Oleynick is a REALTOR® and luxury real estate advisor with Keller Williams Gold Coast in Westport, Connecticut. A frequent News 12 Connecticut real estate expert, she combines extensive local knowledge with more than 20 years of advertising, marketing and media experience. She helps buyers and sellers throughout lower Fairfield County.
