Type to search

These Are the Best Things to Do in Westchester This Week


Our own Wine & Food Fest, multiple Oktoberfests, a drive-in movie, a car show, and a farm-to-table tour top our must-hit list this week.

Westchester has always been home to loads of fun things to do. Whether you’re looking for a fun weeknight activity or something to do once your day off rolls around, we’ve got your shortlist for must-hit plans this week.

Tuesday, September 21

Westchester Magazine‘s Wine & Food Festival is finally here! This week’s events kick off with an incredible Italian wine tasting at Kanopi in White Plains, led by the nation’s leading expert on all things wine (and Hudson Valley resident) Kevin Zraly.

Would you prefer to stay home? If that’s the case, you’re going to love Forever Golden: A Celebration of The Golden Girls. Showcase Cinemas in Yonkers’ Ridge Hill Center and White Plain’s City Center will screen five fan-favorite episodes — “The Pilot,” “The Flu,” “The Way We Met,” “Ladies of the Evening,” and “Grab That Dough” — again this Tuesday at 7 p.m.. Tickets are $14.50, but Betty White is priceless.

Wednesday, September 22

Wine & Food Fest continues with our first-ever Party at the Pier, showcasing some of the county’s top food trucks, along with the best bartenders around facing off to see who can create the ultimate cocktail for our discerning judges.

Thursday, September 23

Break out the elastic waistbands, because W&FF‘s fan-favorite event is back! Burger & Beer Blast will pit two dozen of the top grill masters in Westchester against each other as our audience votes for their favorite burger in the ultimate local cooking competition. Tickets are still available at $75 each, and include all-you-can-eat burgers, drinks, and a few more food truck favorites.


Photo by Heather Sommer

Burke Rehabilitation Hospital will host its virtual 25th Annual Burke Awards at 7 p.m., honoring the organization’s healthcare heroes in a special one-hour ceremony. Tickets include a special gift box, with all proceeds benefiting the organization.

Friday, September 24

Settle in for a more intimate affair, as Yonkers’ X2O hosts another new Wine & Food event, the Wine Collector’s Dinner. Following a champagne reception and charity wine auction, guests will have the opportunity to share their own special bottles and vintages with fellow partygoers along with a decadent dinner prepared by famed Westchester celebrity Chef Peter Kelly. Tickets are $185 per person.

Rather rock out? The Palace Theatre in nearby Stamford will present 1964: The Tribute, an ultimate Beatles lover’s concert recreating the iconic looks and sounds of the pre-Sgt. Pepper era fab four. Tickets start at just $25.

For something a little more kid-friendly, Westchester County’s Movies Under the Stars is back, this week at Tibbetts Brooks Park in Yonkers, screening 2020’s live action Mulan. The show starts at 6:30 p.m. and tickets are $25 per car, drive-in style.

Saturday, September 25

Finally, the climax of our 2021 Wine & Food Fest: The Grand Tasting Village! One $85 ticket gets you access to live chef demos, bites from more than 40 of Westchester County’s hottest restaurants, over 200 wines, food trucks, beer, cider, and spirits, and tons more.

The Stone Barns Center for Food & Agriculture will welcome guests this weekend and next to its returning Harvest Fest. Learn how the farm-to-table process fosters unique relationships between chefs and food as you tour the center’s grounds sampling small bites, plated food, and beverages across the property. Food tours take place every half-hour from 11 a.m. to 3:30 p.m. and last about three hours, with only about 16 guests per session for an intimate experience. Tickets start at $800.


Courtesy Stone Barns Center for Food & Agriculture

This weekend also boasts two of this season’s epic Oktoberfest celebrations. Head to the Hudson for Sleepy Hollow Oktoberfest from 1 p.m. to 5 p.m., then book it up to Bedford for the Sixth Annual Hoppfest at 6:30 p.m. for a double dose of German deliciousness.

If you’re more into art shows than beer fests, this weekend is also the Armonk Outdoor Art Show. Pre-sale tickets are $13 online or $15 at the door to encounter all of the amazing local and regional arts, crafts, foods, and entertainment.

Want to get healthy and give back? Life Time is hosting its inaugural Ride of a Life Time cycling fundraiser for Children’s Miracle Network Hospitals. Registration is free, and classes run at intervals between 8 a.m. and 11 a.m. at both the Harrison and Chappaqua Life Time locations.

Sunday, September 26

Close out your weekend with a little more fun! The Westchester County Car Show returns to Glen Island Park from 9 a.m. to 3 p.m. with more than 100 trophies for different car categories. Registration lasts until noon and parking is $5 for spectators.

Extended Bicycle Sundays are ongoing in Westchester, running from 10 a.m. to 2 p.m. every week (excepting holidays) through October 31. The Bronx River Parkway closes to cars during that time between County Center in White Plains and Scarsdale Road in Yonkers, so make like Freddie Mercury and get on your bikes and ride.


You’ll go out of your *gourd* at the incredible technicolor displays featuring thousands of carved pumpkins at The Great Jack O’Lantern Blaze. Viewing start times run daily through October 31, and then on select days through November 21. Tickets start at about $32 for adults and $24 for kids. Sessions are already selling out on choice holiday and weekend dates even at higher price points, so book your trip fast!

Read More: Croton’s Great Jack O’Lantern Blaze: Everything You Need to Know

The Ronald McDonald House of the Greater Hudson Valley hosts the seventh annual Dashing for Dylan Challenge all month long. Participants can run, walk, bike, canoe, paddleboard, skip, or move any way they want to help raise money for the families of patients staying at Maria Fareri Children’s Hospital in Valhalla.

Want to help your little one explore all the wonder of fall in the Hudson Valley? Teatown Lake Reservation’s Little Tree Huggers program kicks off this week and runs every Tuesday in September from 10:30 a.m. until 11:45 a.m. Ideal for kids about 3 to 5, the program is the perfect opportunity for little ones to hike, experiment in nature, and work on a few projects with the friendly staff as they teach your children what seasonal changes mean. Tickets are $65 per session (or $55 for Teatown members),and groups are limited to eight children each.

Feel like a more challenging hike? You can also get out and enjoy all that Westchester County has to offer without the kids. If you need some suggestions, you can always cross a few destinations off our list of the best hiking and biking trails in Westchester.

Apple picking returns to Westchester and Hudson Valley orchards this month. Use our handy guide to find all the varieties and associated activities your family goes wild for!

stuart's fruit farm apple picking

Photo courtesy of Westchester Land Trust

Farmers’ markets are back! Check our updating guide to keep up with the latest hours and locations for all your favorite spots to shop local in Westchester County.