Pet Parades, Pumpkins & Playdates: Why Fall’s the Best Time to Tour the Suburbs

Oct 16, 2025

Let your four-legged family member strut their stuff at these pet parades in the NYC suburbs

If you’re thinking about making a move, fall is the perfect season to explore potential new hometowns – especially if you’re bringing a furry friend along for the ride. In fact, we’d argue there’s no better time to see a town in action than on a cool October weekend, when community calendars are packed, sidewalks are bustling, and every pumpkin-studded park feels like a movie set.

And for families with four-legged members (or those planning to adopt post-move), pet parades in the NYC suburbs are the perfect excuse to dive into local life. From Westchester to Long Island to Connecticut and New Jersey, fall festivals and Halloween-themed events show off a town’s vibe, values, and pet-friendliness all in one go. Below, we’re rounding up the best pet parades happening this fall so you can tour while your pup struts their stuff.

Westchester County, NY

Rye Brook – HOWL-O-Ween in the Park

  • Date: Saturday, October 25, 2025
  • Time: 10:30 AM – 12:00 PM
  • Location: Pine Ridge Park, 17 Mohegan Lane
  • Why Go: Rye Brook brings the charm – and the adorable pet costumes – with this beloved parade and pet adoption event. Expect lots of families, community groups, and good vibes.

Croton-on-Hudson – HOWL-o-ween Dog Parade

  • Date: Saturday, October 25, 2025
  • Time: Registration at 2:00 PM, Parade at 2:30 PM
  • Location: Croton Landing Park
  • Why Go: A scenic riverside setting makes this parade a stunner. Bonus: there’s a costume contest, raffle, and plenty of local energy.

New Rochelle – Howl’Oween Dog Costume Parade & Contest

  • Date: Sunday, October 18, 2025
  • Time: 10:30 AM – 1:00 PM
  • Location: Ward Acres Park
  • Why Go: This playful event brings the community together with prizes, costumes, and proceeds supporting the Humane Society of Westchester.

Long Island, NY

Old Westbury – Fall Dog Parade & Costume Contest

Date: Sunday, October 26, 2025
Time: 3:00 PM – 5:00 PM (Registration closes at 2:00 PM)
Location: Old Westbury Gardens, 71 Old Westbury Road, Old Westbury, NY

Why Go: As part of Old Westbury Gardens’ popular Dog Days Weekend, this elegant estate throws open its gates to four-legged friends for an afternoon of fall fun. Pups and their owners parade through the grand gardens in full costume — think historic backdrops, crisp autumn air, and endless photo ops. After the parade, a friendly costume contest crowns the most creative canine ensembles. It’s one of Long Island’s most scenic (and tail-wag-worthy) Halloween traditions.

East Meadow – Nassau Barkfest at Eisenhower Park 

  • Date: Sunday, October 26, 2025
  • Time: 1:00 PM – 3:00 PM (Parade & judging start at 2:00 PM)
  • Location: Harry Chapin Lakeside Theatre, Eisenhower Park, East Meadow
  • Why Go: Hosted by the Nassau County SPCA, this free costume contest and pet parade is a can’t-miss for Long Island pet lovers. Expect festive vibes, tons of tail-wagging fun, and a strong showing from the local community. Leashes are required, and guests are encouraged to bring pet food donations to support the SPCA.

Roslyn Harbor – Halloween Pet Parade at Nassau County Museum of Art

  • Date: Saturday, October 25, 2025
  • Time: 2:00 PM – 4:00 PM
  • Location: Nassau County Museum of Art Grounds
  • Why Go: Equal parts art and adorableness, this costumed pet parade comes with live music and autumnal backdrops worthy of a photoshoot.

Fairfield County, CT

Fairfield – Harvest Market & Pet Parade

  • Date: Saturday, October 18, 2025
  • Time: 10:00 AM – 4:00 PM (Pet Parade at Noon)
  • Location: Old Town Green 
  • Why Go: A full fall market with a dog parade? Yes, please. Vendors, food, and local rescues make this the kind of day that shows Fairfield at its finest.

Greenwich – Howl & Prowl 

  • Date: Sunday, October 26, 2025
  • Time: 12:00 PM – 4:00 PM
  • Location: Greenwich Town Hall, 101 Field Point Road, Greenwich
  • Why Go: A beloved annual tradition in Greenwich, this event features a pet costume parade and contest benefiting Adopt-A-Dog. With food trucks, pet-friendly vendors, free samples, and a “haunted sniffari,” it’s a packed afternoon of fall fun. While the event is free to attend, entry into the costume contest is $20, with 100% of proceeds supporting Adopt-A-Dog.

Northern New Jersey

Fair Lawn – Barktober Fest

  • Date: Saturday, October 25, 2025
  • Time: 12:00 PM – 3:00 PM 
  • Location: Memorial Park River Walk
  • Why Go: This ticketed event (just $7!) includes a dog costume contest with prizes and a whole lot of local flair.

Montclair – Strut Your Mutt

  • Date: Saturday, October 25, 2025
  • Time: 9:30 AM start (Registration at 9:00 AM)
  • Location: Brookdale Dog Park
  • Why Go: Montclair families take Halloween seriously, so expect top-tier costumes and major community energy.

Why We Love Pet Parades in the NYC Suburbs

Yes, it’s fun. But these events do more than deliver a cute photo op—they give you a real feel for the community. You’ll get to see how family-friendly the sidewalks, parks, and town centers are, watch how people show up for local events, chat with future neighbors (especially other pet parents), and get a sense of how walkable the area is, from dog parks to rec centers and beyond.

Ready to explore the suburbs with your furry sidekick? Let’s talk! Schedule your free initial strategy call today. 

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