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Explore the NYC Suburbs Like a Local!

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We can’t believe September is almost over…but there’s still plenty of time to get out and check out the suburbs before the temperature drops.

 

While it might not feel like it, fall is officially here—and we’re counting down to scarves, fire pits and all things pumpkin spice. 

 

We’re also loving the early fall slate of activities and events in the NYC suburbs. Not only are they a fun way to spend the weekend with your crew, they’re also a great way to explore suburbia. Check out the list!

 

Looking in other towns? Get in touch and we’ll help strategize your perfect weekend!

 

 

HEADING TO WESTCHESTER?

Chappaqua

The Chappaqua Farmers Market is from 8:30am-11:30am on Saturday. Shop and sample local produce, cheese, meats, prepared foods and even flowers and household goods from dozens of area vendors, farmers and makers. 

 

 

Rye

Fall into Fun with Rye Playland! The event is happening Saturday and Sunday from 1pm-7pm. Admission to the “main” park for rides and games is $15, plus there will be pumpkin picking and painting, a DJ and face painting onsite.

 

 

Rye Brook

Head to Crawford Park for the Dylan J. Hoffman Walk & Family Fun Day, taking place from 10am-2pm on Sunday. Afterward, there will be inflatables, the BASF Kids Slime Lab, a DJ and other family-friendly activities.

 

 

Armonk

Pack up the kids and join the Eugene and Agnes Meyer Nature Preserve Hike starting Sunday at 9:30am. The hike is three miles and kicks off from the West Parcel Area. The easy-to-moderate hike is hosted by Latinas Who Hike.

 

 

Bedford

Bedford’s Fire on the Green is Saturday from 3pm-8pm at the Village Green. The event features live music, inflatables, games, food trucks and more. Admission is $5. 


For DIYers and foodies out there, there’s also a hands-on canning, pickling and cooking class for families from 10am-1pm at Sugar Hill Farm in Bedford Hills.

 

 

Katonah

Learn about wildlife and explore nature at Muscoot Farm’s “forest exploration” on Saturday from 1pm-3pm.

 

 

Larchmont/Mamaroneck 

Larchmont’s Hommocks Park Ice Rink opens for the season on Saturday. The opening kicks off with a public skate from 1pm-4pm.

 

In Mamaroneck, visit the public library on Saturday for stories and a craft starting at 11am.

 

 

Scarsdale/Edgemont 

Learn about local critters with the Greenburgh Nature Center from 1pm-2pm on Saturday. Admission is $8 for non-members.

 

 

Ardsley

The Ardsley Fire Department Carnival is Tuesday through Sunday, with extending hours on Saturday and Sunday. Single tickets are $1.25.

 

 

Pleasantville

Watch featured films from the NY Children’s Film Festival from 12pm-1pm on Sunday at the Jacob Burns Film Center. The short films are ideal for children ages 3-7.

 

 

Ossining 

The Maryknoll Sisters Fall Festival in Ossining is happening from 11am-4pm on Saturday. This is a great event for kids and includes tons of local food trucks, a bubble show, live music, exotic animals and more.

 

 

HEADING TO LONG ISLAND?

Roslyn

Visit Studio Saturdays at the Manes Center for hands-on kids crafts from 12pm-3pm on Saturday. Museum admission is required.

 

 

Port Washington

There’s a huge Greek festival in Port Washington Friday, Saturday and Sunday afternoons, featuring live music, rides, a flea market and games. This end-of-season carnival-style event is perfect for families who want to squeeze in one more ride before summer really ends—and the homemade Greek food is amazing. 

 

 

Sea Cliff 

The Sea Cliff Farmers Market is at 9am Saturday. Stop by to explore downtown and pick up some local produce, artisanal cheese and meat, flowers, gourds and other treats.

 

 

Manhasset

Get crafty in Manhasset this weekend, while also getting ready for Halloween. Your kids can make a Jack-o’-Lantern pumpkin from 11am-2pm on Saturday at Michaels in Manhasset. 

 

 

HEADING TO NEW JERSEY?

Morristown 

The Crimson Fall Family Festival is from 11am-1pm on Saturday at the Morristown-Beard School campus. Swing by for refreshments, a DJ and photo booth, snacks, pumpkin painting, face painting and a giant slide.

 

 

Millburn 

Saturday is Rocktoberfest in Millburn. Come out for live music, rides, games, seasonal treats, STEM activities and more from 9am-11:45pm.

 

 

Montclair 

Montclair’s Fall Fest and Duck Derby is Saturday. For $10, race yellow ducks to win prizes, all while enjoying live music, face painting and other kids’ attractions. From 2pm-4pm, there’s also mommy & me slime-making workshop in town for families who don’t mind getting their hands dirty. 

 

For local beer fans, Montclair Brewery is hosting a family-friendly Oktoberfest event on Saturday starting at 7pm. Here, they’ll release a special seasonal lager plus Bourbon Barrel aged brown ale. The outdoor festival will also include food vendors, crafts for kids and live music. 

 

 

Glen Ridge 

The Glen Ridge Friends of the Library group is hosting a town-wide yard sale on Saturday from 9am-4pm. It’s the perfect opportunity to explore the community and hunt for great vintage finds to fill your new home.

 

 

Demarest 

Visit Demarest Farms at 5:30pm on Friday for a special movie night accompanied by pumpkin picking, hayrides, a petting zoo and more.

 

 

Summit 

Visit Reeves-Reed Arboretum to learn about wildlife on Saturday from 9am-1pm or Sunday for an Oktoberfest from 1pm-5pm. Or, visit the town’s farmers’ market for Sunday Funday and an apple pie contest from 11am-12pm.

 

 

HEADING TO CONNECTICUT? 

Westport 

Get ready to be amazed at this annual hot air balloon festival and polo match in Westport from 7am-9pm on Saturday.

 

 

Darien 

Have a little builder? They’ll love LEGO Club at Darien Library from 2pm-4pm, open to children ages 5 and up.

 

 

Greenwich 

There’s a pet festival at Roger Sherman Baldwin Park from 10am-4:30pm on Sunday. You can see adoptable pets, plus enjoy kids’ games and food trucks.

 

 

Wilton

The Cannondale Fall Foliage Festival starts at 11am on Saturday and Sunday. Check out local vendors and plenty of area shopping. 

 

 

Stamford

Check out the Stamford Greek Festival Thursday through Sunday for carnival rides, games, vendors and Greek cuisine.

 

 

Norwalk/Rowayton 

Visit Ripka’s Beach Cafe for Beach Oktoberfest from 3pm-8pm on Saturday.

 

 

There are hundreds of towns to choose from. How do you figure it all out? You simply don’t, without getting a Suburban Jungle Strategist to help you through it all. Schedule here for your strategy session with our innovative suburbs strategy team. All services are completely free.

 

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