Fall activities in Westchester County worth doing this year

Fall in Westchester is when the county actually earns the hype. The leaves do the thing, the air stops being soup, and suddenly everyone wants to be outside again. If you spent the summer alternating between AC and pool days, welcome back.

Here is what is worth doing this fall, whether you are looking for something low key on a weekday evening or a full weekend plan.

Apple picking and cider

Obvious, but still good. Harvest Moon Farm and Orchard in North Salem and Stuart’s Fruit Farm in Granite Springs are the go-to spots. Go on a weekday if you can. Weekends in October are a zoo. Stuart’s has a cider donut situation that people drive from the city for, and honestly it is worth it.

Wilkens Fruit and Fir Farm in Yorktown is another solid pick if you want something a little less crowded. They do hayrides too.

Fall festivals and outdoor markets

Westchester goes hard on fall festivals. The Sleepy Hollow Music Festival, Harvest Mess and Music Fest, and the Great Jack O’Lantern Blaze in Croton are the big ones. The Blaze sells out, so get tickets early if you have not been.

For something smaller, check the farmers markets in Pleasantville and Ossining. Both run through November and the fall produce selection is way better than summer. The Tarrytown Halloween parade is also worth seeing at least once.

Untermyer Gardens in Yonkers is another one worth adding to the list. The Persian-style gardens look incredible in the fall and it is free. Rivertowns in general are the move in October. Sleepy Hollow and Tarrytown lean all the way into the Halloween thing and it is genuinely fun, not just for kids.

Hiking with actual views

Fall hiking in Westchester is a different experience from summer hiking. The trails are less muggy, the views are better, and you can go past noon without melting. Rockefeller State Park in Pleasantville has wide carriage paths that are perfect for a walk with friends. Cranberry Lake Preserve in White Plains is smaller but quieter.

If you want something with more of a payoff, drive up to Bear Mountain or Breakneck Ridge. Not technically Westchester but close enough, and the fall colors from the top are worth the drive.

We wrote a whole post on the best hikes in Westchester if you want more options.

Outdoor fitness before winter hits

Fall is the sweet spot for outdoor workouts. The humidity is gone, the mornings are cool, and you can exercise past 9 AM without overheating. Outdoor yoga classes pop up at parks around the county in September and October, and pickleball courts at places like Saxon Woods and Rye Town Park are packed on weekends.

If you are looking for something more casual, the walking paths at Kensico Dam Plaza and the Bronx River Pathway are perfect for a long walk with a friend. The scenery gets better every week as the colors change.

Wine tastings and cocktail bars

Fall cocktail menus are the best cocktail menus. The Birdsall House in Peekskill does seasonal drinks and has a patio that is perfect in October. Pubstreet in Dobbs Ferry is a good option if you want cocktails without a reservation. Faccia Luna in Tarrytown does wine nights that are worth checking out.

For actual wine tasting, a few of our members have done day trips to the Hudson Valley wineries (Millbrook, Whitecliff, Brotherhood) and the drive alone is worth it in fall.

Outdoor dining before it is too late

October is the last real month for outdoor dining before the heaters come out and it gets questionable. The brunch spots with patios fill up fast on weekends. We put together a list of the best brunch spots in Westchester that covers a lot of the good outdoor options.

If you are looking for dinner, Mulino’s in White Plains has a terrace, and some of the Tarrytown spots along the waterfront are great for a fall evening.

Volunteering and community events

Fall is also a good time to get involved. Food drives pick up in October and November, the Yonkers waterfront has cleanup days, and a lot of local nonprofits run their biggest fundraisers in the fall. We have done group volunteer days with our members and they are always one of the more rewarding events on the calendar.

What Club West is doing this fall

We have a packed fall calendar. Coming up next:

Cafecito Social on Friday, September 25th at Nuna Harvest in Mount Vernon. It is a BYOB sip and paint where you customize your own stovetop greca with a Latin-inspired playlist and plenty of cafecito. All supplies included. Get tickets on Eventbrite.

Club West’s 1-year anniversary gala on Saturday, October 3rd at The Fairways at Dunwoodie Golf Course in Yonkers. Dinner, dancing, and a year of reasons to celebrate. Dressy, 21+, open to everyone. Get tickets on Eventbrite.

Beyond those, we have weekly fitness events, happy hours across the county, seasonal parties, and regular brunch outings all fall. Members also organize their own meetups through our Discord, like apple picking trips, group hikes, and pumpkin carving nights.

Membership is $10 a month. If you have been thinking about joining, fall is a good time. The calendar is packed and the energy picks up. Apply for membership or follow @clubwestofficial on Instagram for event announcements.

Common questions about fall in Westchester

When does fall foliage peak in Westchester County?

Most years, peak color hits the northern part of the county (Bedford, Katonah, Pound Ridge) in mid to late October. The southern towns along the river, like Hastings and Dobbs Ferry, tend to peak a week or so later because of the warmer microclimate near the Hudson. Bear Mountain and Harriman State Park, just north of the county line, usually peak around the second or third week of October.

What are the best fall festivals in Westchester?

The Great Jack O’Lantern Blaze at Van Cortlandt Manor in Croton-on-Hudson runs from mid-September through mid-November. Jay Heritage Center in Rye does an Oktoberfest. Harvest Fest at Hilltop Hanover Farm in Yorktown Heights has hayrides and apple cider donuts. Cross County Shopping Center in Yonkers runs fall markets most weekends in October. The Pleasantville Music Festival, if it falls early enough, sometimes catches the last warm weekend of September.

Where can you go apple picking near Westchester?

Harvest Moon Farm and Orchard in North Salem and Salinger’s Orchard in Brewster are the two closest options with a good variety of apples. Stuart’s Fruit Farm in Granite Springs does pick-your-own too. Weekends in late September and early October get crowded at all three, so go early or try a weekday if you can. Most orchards charge by the bag, usually around $15-25 depending on size.

Is Westchester worth visiting in fall if you are not from the area?

Honestly, yes. The train from Grand Central gets you to the Hudson River towns in under an hour, and the foliage along the Metro-North line from Tarrytown to Cold Spring is one of the better fall train rides in the Northeast. You can do a day trip with Kykuit (the Rockefeller estate) in the morning, lunch in Tarrytown, and the Blaze at night. Just book everything in advance because October weekends sell out.