September-November 2026: the local events actually worth putting on your calendar.
Fall here is not one thing. It is serious art in Armonk, children lining up for authors in Chappaqua, a moonlit mansion in Tarrytown, pumpkins at Muscoot and history coming alive in Pound Ridge. This is the list I would send a friend, organized by date and edited for the days that feel specific to Westchester and the lower Hudson Valley.
A local note: Event hours, prices and ticket rules can move. Click the official link before you get in the car.
Saturday, September 19
New Castle Community Day | Chappaqua
The fall calendar starts with the kind of day that reminds you why people move here: local booths, neighbors running into neighbors, kids finding each other before you do. This is a true Chappaqua community day, not a generic “festival” dropped into a parking lot.
September 19, 2026. The Rotary organizer page confirms the date; recheck the page for public hours and final visitor details before posting.
Friday, September 18-November 8
The Great Jack O’Lantern Blaze | Croton-on-Hudson
Yes, Blaze is famous. It is also still one of the rare blockbuster fall events that feels specific to the Hudson Valley. My advice: choose an early-season weeknight if you care more about wandering than fighting a crowd.
Select evenings September 18-November 8, 2026 at Van Cortlandt Manor. Advance tickets required; none sold on site. Timed entry starts at $24; premium options cost more.
Thursday-Sunday, September 24-27
Discover Boating Norwalk Boat Show | Norwalk, CT
This is the one Connecticut detour I am making, because Norwalk is an easy day trip from lower and central Westchester. You do not need to be shopping for a boat. The marina setting, demos and on-water energy make it feel like one last glamorous weekend of summer.
September 24-26, 10 a.m.-7 p.m.; September 27, 10 a.m.-5 p.m. Norwalk Cove Marina. Adults $20; ages 13-17 $10; 12 and under free with a paid adult. Box office is cashless.
Saturday, September 26
Chappaqua Children’s Book Festival | Chappaqua
This is a Westchester bragging-rights event. The author lineup is the draw, but the real magic is watching kids treat books like celebrities. Make time for the tables you do not recognize; that is usually where you find the book everyone is talking about later.
Saturday, September 26, 2026, 10 a.m.-4 p.m., Chappaqua Train Station. Free admission. Rain or shine. The official 2026 listing is one day, not September 26-27.
Saturday-Sunday, September 26-27
Armonk Outdoor Art Show | Armonk
This is not a craft fair pretending to be an art show. About 160 juried artists come in from around the country, and people actually buy serious work here. Go early, wear shoes you can stand in, and leave time for lunch in town.
September 26-27, 2026, 10 a.m.-5 p.m., rain or shine. 205 Business Park Drive. Tickets are sold online and at the show; 18 and under free. No dogs. Check current adult ticket price.
Saturday, September 26
Greeley Farm Walking Tour | Chappaqua
A smart little palate cleanser if you want something quieter than a festival. The walk traces parts of Horace Greeley’s original 78-acre farm and gives downtown Chappaqua a whole different shape once you know what you are looking at.
The Historical Society lists the 2026 walking-tour series September 12-26. Check the September 26 departure time, price, capacity and reservation status directly before publishing.
Sunday, October 4
Cider & Donut Festival + Jamie’s 5K Run for Love | Armonk
Cider, donuts, a 5K and a hometown carnival is basically the North Castle fall starter pack. If you are not running, come for the community scene. If you are running, you have fully earned the donut.
Sunday, October 4, 2026 at Wampus Brook Park. Festival admission is free; race registration is separate. Check exact festival and race times and current registration fees.
Saturday-Monday, October 10-12
Pumpkin Picking Weekend | Muscoot Farm, Katonah
This is my pick when you want pumpkins without turning the entire day into an agritainment operation. The free farm programming keeps it local and low-pressure; pumpkins, hayrides, cider and donuts support the Friends of Muscoot Farm.
October 10, 11 and 12, 2026, 10:30 a.m.-3:30 p.m. Free entrance; pumpkins, hayrides, cider and donuts available for purchase.
Thursday-Sunday, October 15-18
ArtsFest | New Rochelle
Four days is exactly right for New Rochelle because the point is to move around. Galleries, studios and performance spaces open up across the city, which makes this feel more like an arts crawl than a single fenced-in event.
October 15-18, 2026. Schedule, individual venue hours, admission and reservation rules vary by program; check each event you plan to name.
Saturday-Sunday, October 17-18
Trick-or-Treat Weekend at Lyndhurst | Tarrytown
Lyndhurst understands Halloween atmosphere. The mansion and grounds do most of the decorating for you. This one works when the kids want candy but the adults would also like architecture and a real sense of place.
October 17-18, 2026. Grounds pass: $15 general admission, kids 10 and under free. Mansion-entry tickets cost more. Check hours and remaining ticket inventory.
Sunday, October 18
Castles of New Castle Historic Houses Tour | Chappaqua
This is the insider pick for anyone who slows down to look at an old house. A handful of private historic homes open for one day, which means architecture, interiors and just enough nosiness to make it fun.
Sunday, October 18, 2026, 11 a.m.-4 p.m. Tickets were slated to go on sale in August; check price, availability and meeting/check-in details.
Select nights, October 2-31
Twilight Village at Sleepy Hollow | Philipsburg Manor
Come for the Headless Horseman mythology, stay because this is one of the better all-ages ways to do Sleepy Hollow after dark. It has performers, atmosphere and enough going on that nobody is simply waiting in a line to be scared.
Select nights October 2-31, 2026. Hours vary: 6:30-8 p.m. on Oct. 2 and 4; 6:30-9 p.m. Oct. 3, 9-11 and 16-18; 6-9 p.m. Oct. 23-25 and 30-31. $25-$35. Advance tickets only.
Saturday-Sunday, October 24-25
REV FEST 250 | Ward Pound Ridge Reservation
This is the event I would circle for northern Westchester. A large-scale Battle of White Plains reenactment inside Ward Pound Ridge Reservation is very specific, very local and wildly more interesting than another row of pumpkin vendors. Bring layers. The reservation always feels a few degrees cooler than the parking lot.
October 24-25, 2026, 10 a.m.-4 p.m. Free admission. Check parking, accessibility, shuttle rules and the final reenactment schedule.
Saturday, October 24
Tarrytown Halloween Parade | Tarrytown
The parade is loud, homemade, crowded and exactly the point. Do not improvise parking at 4:55. Make a dinner plan, arrive early and treat the whole village as the event.
Saturday, October 24, 2026, 5-10 p.m. Parking will be extremely limited because of road closures. Check parade step-off time and route before publishing.
Saturday, October 31
Boo Walk | Muscoot Farm, Katonah
For younger kids or anyone who prefers cute to terrifying, this is the Halloween answer. Costumes on, non-scary woodland trail, done by mid-afternoon.
Saturday, October 31, 2026, noon-3 p.m. The walk closes promptly at 3. Check admission/reservation policy.
Saturday, November 7
Westchester Book Festival | Katonah
Katonah is already a very good place to spend a Saturday, then add bestselling authors, talks, signings and local shops. Build in time to wander between venues instead of treating this like one auditorium event.
Saturday, November 7, 2026 in Katonah. Tickets are needed for individual sessions at Katonah Village Library and Katonah Presbyterian Church. Check session prices, sellouts and full schedule.
Saturday, November 21
Holiday Market | Pound Ridge
This one gets the StacyKnows hometown seal. Pound Ridge does small and beautiful especially well, and this is where I would look for a hostess gift that does not feel mass-produced. Go early, then make a full morning of Scotts Corners.
Saturday, November 21, 2026, 10 a.m.-4 p.m., 77 Westchester Avenue, Pound Ridge. Check final vendor list, admission and weather policy.
Saturday, November 21
Hudson Valley Music Summit | Chappaqua
Not every fall guide needs to end in a pumpkin patch. This is the practical, industry-facing pick for musicians, managers and the people trying to understand what the business looks like now.
Saturday, November 21, 2026 at Chappaqua Performing Arts Center. Agenda begins with 8:30 a.m. registration and concludes around 4:30 p.m.; mentoring runs 9 a.m.-5 p.m. Check ticket price, availability and any separate evening showcase admission.
If you only choose five
New Castle Community Day for hometown energy. The Chappaqua Children’s Book Festival because it is genuinely special. The Armonk Outdoor Art Show for grown-up browsing. REV FEST 250 because Ward Pound Ridge is our backyard and this one will not come around in quite the same way again. The Pound Ridge Holiday Market for the gifts you will actually be happy to give.
