A hometown festival, a two-for-one Yonkers day, fall shopping, history, flowers, family fun and a very Sleepy Hollow Sunday.
If you have been waiting for a weekend that makes the case for staying local, this is it. Westchester is packed, from Bedford’s big hometown gathering to Yonkers on the river and the first real taste of Sleepy Hollow season. My plan? Pick one anchor event, add one nearby extra, and leave a little room for lunch.
Saturday’s hometown lead: Bedford Tri-Festa
Saturday, September 19, 2026, 3-8 p.m.; Bedford Village Memorial Park, 65 Greenwich Road, Bedford; free admission.
This is the hometown headliner. Bedford’s three hamlets come together for live music, food trucks, family attractions and community groups, with a Rev Up 250 theme in the mix. It is easy, festive and close enough that Bedford people can run into half the town before dinner.
Stacy’s take: Start here if you want the true local-scene choice. It is the kind of afternoon that turns into an accidental reunion every ten feet.
Also close to home: New Castle Community Day
Saturday, September 19, 2026; Chappaqua.
One more for Saturday, and this one is pure Chappaqua: New Castle Community Day. This is the hometown stop for community groups, local organizations and the kind of neighbor-to-neighbor catching up that turns a quick visit into half the afternoon. If you are already building a northern Westchester day, put this before Bedford Tri-Festa and call it a very local double-header.
The best double-header: history plus Riverfest in Yonkers
Two free events within downtown Yonkers make this the smartest full-day plan. Do the historic stop first, then walk toward the music, food and waterfront energy.
Revolutionary Harvest Festival at Philipse Manor Hall
Saturday, September 19, 2026, noon-5 p.m.; Philipse Manor Hall State Historic Site, 29 Warburton Avenue, Yonkers; free.
The grounds go Revolutionary for the day with costumed reenactors, living-history demonstrations, cider pressing, colonial crafts, music, dancing, games and a family espionage activity. This is the rare history event that gives adults plenty to see while children have something to do with their hands.
Yonkers Riverfest
Saturday, September 19, 2026, noon-7 p.m.; 1 Larkin Plaza and the downtown Yonkers riverfront; free admission.
Westchester’s largest one-day festival fills downtown and the waterfront with music, food, vendors and family fun. It is big enough to wander, snack and catch more than one stage without making the day feel scheduled to death.
Stacy’s take: Pair it with Philipse Manor Hall. History first, festival food second, Hudson views throughout.
More Saturday picks
Hudson Valley Irish Festival, Peekskill
Saturday, September 19, 2026, 11 a.m.-7 p.m.; Riverfront Green Park, Peekskill; tickets offered online.
Irish music, food, crafts and plenty of green on the Hudson for this halfway-to-St. Patrick’s Day celebration. A good pick for anyone who wants live music to carry the whole afternoon.
Fall Crafts at Lyndhurst, Tarrytown
Saturday, September 19, 10 a.m.-6 p.m.; Sunday, September 20, 10 a.m.-5 p.m. Advance online: $13 general, $12 seniors 62+, $6 ages 6-16, under 6 free, plus fees. Gate prices are higher; cash only. Rain or shine.
More than a quick craft stop, this is a day on the Lyndhurst grounds: juried makers, fashion, jewelry, home decor, gourmet food, tastings, demonstrations and children’s activities. The Gothic mansion in the background does not hurt.
The Silk Road Flower Show at Lasdon
Saturday, September 19, 2026, 9 a.m.-3:15 p.m.; Main House at Lasdon Public Gardens, 2610 Amawalk Road, Katonah.
Floral design and horticultural exhibits draw inspiration from the Silk Road. This is the calm, beautiful choice, and an easy morning outing before Bedford Tri-Festa.
Ganesha Festival at Hammond Museum, North Salem
Saturday, September 19, 2026, noon-4:30 p.m.; Hammond Museum & Japanese Stroll Garden; festival free with museum admission; RSVP listed.
An afternoon of Indian dance and culture celebrating Ganesha, set inside one of Northern Westchester’s loveliest small museums and gardens.
STEAM Fair at Ossining Public Library
Saturday, September 19, 2026, 11:30 a.m.-1:30 p.m.; Budarz Theater, Ossining Public Library.
The Westchester Children’s Museum brings hands-on science, technology, engineering, art and math stations for children in kindergarten and older. A solid two-hour plan for curious kids.
TEAC Eco Fair at The TaSH, Tarrytown
Saturday, September 19, 2026, 10 a.m.-1 p.m.; Patriots Park during The TaSH Farmers Market; free. September 27 rain date.
Shop the farmers market while meeting local environmental groups and learning practical ways to make home and community a little greener. This is an easy add-on rather than an all-day commitment.
Sunday: lean into Sleepy Hollow season
Sunday’s best plan is classic river-town fall: start on Beekman Avenue, then head toward the Hudson for the lighthouse. If reservations disappear, keep the street fair as the anchor and save the lighthouse view for a walk.
Sleepy Hollow Street Fair
Sunday, September 20, 2026, 10 a.m.-5 p.m.; Beekman Avenue, Sleepy Hollow; free; rain or shine.
Beekman Avenue fills with more than 145 vendors, local shops, family entertainment, live music, a kids’ zone and plenty of Halloween-inspired finds. The Headless Horseman is scheduled to appear from 1 to 4 p.m., because Sleepy Hollow knows exactly what month is coming.
Stacy’s take: Go early for easier browsing, stay for lunch, and do not pretend you are leaving without at least one pumpkin-shaped thing.
Tarrytown Lighthouse tours
Sunday, September 20, 2026, 10 a.m.-2 p.m.; free; advance reservations required.
The 1883 cast-iron lighthouse is one of those landmarks many Westchester people have looked at for years without ever going inside. Timed tours make this the perfect Sunday add-on if you can grab a reservation.
Also Sunday: Fall Crafts at Lyndhurst
Sunday, September 20, 2026, 10 a.m.-5 p.m.
Miss Saturday? Lyndhurst runs for a second weekend day, which also makes it an easy alternative if the lighthouse tour is full.
Stacy’s three easy weekend plans
- Close to home: The Silk Road Flower Show in Katonah, then Bedford Tri-Festa.
- All-day energy: Revolutionary Harvest Festival, then Riverfest in downtown Yonkers.
- Peak September: Sleepy Hollow Street Fair, a reserved lighthouse tour and, if you still have steam, Lyndhurst.
Whatever you pick, check the linked event page before you get in the car. Times, ticket inventory and weather plans can move quickly. Then go enjoy the rare Westchester weekend when the hard part is narrowing it down.
