The Ultimate Hudson Valley Dog Halloween Event Guide (2026) 🎃🐾

Crisp mountain air, crunching amber leaves underpaw, and pups strutting through historic downtowns dressed as pumpkins, bats, and hot dogs—spooky season in the Hudson Valley is officially here!

At Pawsitive Spots, we believe our four-legged family members deserve to join in on every seasonal adventure. From lively waterfront puppy parades to vineyard costume parties and cozy shop trick-or-treating, our region is packed with tail-wagging ways to celebrate Halloween.

Grab your leash, dust off your pup’s favorite disguise, and check out our county-by-county roundup of dog Halloween parades, costume contests, and harvest festivals across the Hudson Valley!

🐶 Dedicated Dog Parades & Costume Celebrations

Dutchess & Columbia Counties

🎃 Lilly’s Natural Pet Store Howl-O-Ween Costume Contest

When: Saturday, October 24 & Sunday, October 25, 2026 | 11:00 AM – 6:00 PM both days
Where:
- 📍 Poughkeepsie: 930 Dutchess Turnpike (Eastdale Village), Poughkeepsie, NY
- 📍 Hudson: 76 N 7th Street, Hudson, NY
What to Expect: A weekend-long celebration across two wonderful storefronts! Bring your leashed pup in costume to snap a keepsake picture at their festive Halloween photo spot and pick up a complimentary swag bag (one per dog, while supplies last). Handlers can scan the in-store QR code to submit their dog’s photo for the online costume contest, where community voting will decide the winners for Funniest, Spookiest, and Most Creative looks!
Admission: Free to enter; no purchase necessary. Dogs must remain leashed.

🍸 Howl-o-ween at Denning’s Point Distillery

When: Late October / Seasonal Weekend (Check venue calendar)
Where: 10 N Chestnut Street, Beacon, NY
What to Expect: Beacon’s popular craft distillery pairs up with the Animal Rescue Foundation (ARF) for a seasonal costume gathering. Sip locally distilled spirits while socializing with costumed pups in support of local shelter rescues.

Westchester & Rockland Counties

🐕 Howl-o-Ween Dog Parade & Costume Contest

When: Saturday, October 24, 2026 | Registration at 2:00 PM, Parade steps off at 2:30 PM
Where: Croton Landing Park, Elliott Way, Croton-on-Hudson, NY
What to Expect: A scenic parade along the Hudson River featuring a judged costume competition, raffles, and seasonal prizes.
Good to Know: Admission is free with on-site registration. Dogs must be licensed, vaccinated, and socialized. (Note: Make sure to attend this afternoon parade, not the morning village Goblin Walk, which asks families to leave pups at home!)

🐾 Town of Cortlandt Halloween Dog Parade

When: Saturday, October 24, 2026 | 2:30 PM sharp
Where: Cortlandt Dog Park at Sprout Brook Park, 130 Sprout Brook Road, Cortlandt Manor, NY
What to Expect: Held directly inside the town’s fenced dog park, this parade lets dogs play and show off their festive outfits in a secure off-leash environment with treats for participants. Free admission; contact Cortlandt Recreation (914-734-1050) with questions.
Pawsitive Tip: Because Croton-on-Hudson and Cortlandt Manor share a 2:30 PM start time on October 24, pick the setting your pup prefers—a riverfront walk or an enclosed dog park playdate!

👻 Howl’oween Dog Parade & Costume Contest at Ward Acres

When: Saturday, October 17, 2026 | 10:30 AM – 1:00 PM (Parade begins at 11:00 AM)
Where: Paws Place Dog Park at Ward Acres Park, Quaker Ridge Rd & Sussex Rd, New Rochelle, NY
What to Expect: A costumed canine parade and competition judged by Humane Society of Westchester volunteers. Donations of canned food and treats are collected at check-in to support shelter pets. Limited on-site registration available.

🍂 Lewisboro Howl-O-Ween Pet Parade

When: Saturday, October 17, 2026 | 1:30 PM – 2:30 PM
Where: Lewisboro Town Park, 1079 Route 35, South Salem, NY
What to Expect: A classic community pet stroll with costume judging and goodie bags.

🦴 White Plains Howl-o-Ween Bash

When: Saturday, October 24, 2026 | 11:00 AM – 12:00 PM
Where: Bark Dog Park on Brockway Place, White Plains, NY
What to Expect: A neighborhood dog park Halloween meetup for four-legged trick-or-treaters.

🎃 Bark ’n Brews Howl-O-Ween Party

When: Saturday, October 31, 2026 | 12:00 PM – 5:00 PM
Where: 35 Smith Street, Nanuet, NY
What to Expect: Celebrate Halloween afternoon with spooky photo ops, seasonal drinks, and indoor canine socialization.

Ulster & Orange Counties

🏆 HOWL-A-WEEN Doggy Costume Contest & Parade

When: Saturday, October 24, 2026 | Check-in 10:00 AM – 11:45 AM, Parade at 12:00 PM
Where: Hudson Valley Open Market at New Paltz Middle School, 196 Main Street, New Paltz, NY
What to Expect: The 3rd annual community runway parade and costume competition awarding 1st and 2nd place prizes, paired with raffles benefiting Bleu’s K9 Rescue.
Good to Know: Free entry; donations encouraged. Each dog requires an adult handler (18+) on a 4–6 foot standard leash (no retractable leashes).

🍷 Pawstume Party at Whitecliff Vineyard

When: Saturday, October 24, 2026 | All-Day (Call 845-255-4613 for schedule)
Where: 331 McKinstry Road, Gardiner, NY
What to Expect: Sip estate wines overlooking the Shawangunk Ridge while your pup struts their stuff! A seasonal costume party and fundraiser supporting the Walden Humane Society.

🍕 Starlite Motel Halloween Pet Parade

When: Friday, October 31, 2026 | 5:00 PM – 10:00 PM
Where: Starlite Motel, 5938 Route 209, Kerhonkson, NY
What to Expect: Retro Catskills charm meets Halloween! Enjoy vinyl DJ sets, wood-fired pizza, a costumed pet parade, and raffles supporting the Ulster County SPCA.

🎪 Fall Festivals with Dedicated Pet Costume Divisions

🍎 Tract-or-Treat at Barton Orchards

When: Saturday–Sunday, October 24–25, 2026 | 10:00 AM – 6:00 PM (Parade lineup at 3:30 PM, Contest at 4:00 PM)
Where: Barton Orchards, 63 Apple Tree Lane, Poughquag, NY (Dutchess County)
Dog Highlights: A full harvest festival featuring a dedicated Best Dog Costume division in the daily contest! Pups can also play in Barton’s 5,000-sq.-ft. fenced dog park. Leashed dogs are welcome on farm grounds (excluding buildings, maze, and haunted house).
Admission: Tickets start at $34 (ages 13+) / $22 (ages 4–12); check online for early-bird savings.

🎭 37th Annual Nyack Halloween Parade

When: Saturday, October 24, 2026 | 5:30 PM – 7:30 PM (Rain date: October 25)
Where: Main Street & Broadway, Nyack, NY (Rockland County)
Dog Highlights: Rockland County’s marquee parade explicitly welcomes leashed, costumed pets to march alongside colorful floats, fire trucks, and bands.

💫 Walk for Wishes Family Fun Day

When: Sunday, October 25, 2026 | 9:00 AM – 2:00 PM (Walk steps off at 11:00 AM)
Where: Kingsland Point Park, 299 Palmer Avenue, Sleepy Hollow, NY (Westchester County)
Dog Highlights: A riverside charity walk benefiting Make-A-Wish Hudson Valley featuring music, food trucks, and a judged pet costume contest.

🍭 Warwick Halloween Parade

When: Saturday, October 31, 2026 | Lineup at 4:30 PM, Parade at 5:00 PM
Where: High Street down to Railroad Avenue, Warwick, NY (Orange County)
Dog Highlights: A beloved village tradition where families and costumed canines stroll Main Street together for community costume judging.

🍂 Wurtsboro Hallow-Harvest Fest

When: Saturday, October 31, 2026 | 12:00 PM – 3:00 PM
Where: Sullivan & Third Street / Veterans Park, Wurtsboro, NY (Sullivan County)
Dog Highlights: Small-town harvest games, candy stations, and an open pet costume parade.

🏕️ Blackthorne Resort Trunk-or-Treat

When: Halloween Weekend (October 30 – November 1, 2026; call 518-634-2541 for dog parade schedule)
Where: Blackthorne Resort, 348 Sunside Road, East Durham, NY (Greene County)
Dog Highlights: Free family Trunk-or-Treat event featuring a pet costume contest and dog parade.

🏛️ Capital Region Spotlight: Albany & Troy

🐾 Hounds of Halloween & Yappy Hour

When: Saturday, October 17, 2026 | 12:00 PM – 4:00 PM (Yappy Hour: 4:00 PM – 6:00 PM)
Where: Check-in at Quackenbush Square; Puppy Parade at Clinton Market Collective (11 Clinton Ave, Albany, NY)
What to Expect: Downtown trick-or-treating for pups at local storefronts, official Canine Costume Contest judging, a 3:30 PM Puppy Parade, and patio Yappy Hour drink specials.
Admission: $15 advance / $20 day-of per dog, benefiting the Mohawk Hudson Humane Society.

🐕 The Barkwalk Howl-o-Ween

When: Saturday, October 10, 2026 | 1:00 PM – 4:00 PM
Where: Troy, NY
What to Expect: Costumed pups take to the runway to compete for Best Costume and Best Look-Alike, alongside pet-friendly local vendors and shelter adoption desks.

🐾 Pawsitive Tips for a Safe & Spooky Outing

Test the Fit at Home: Ensure costumes don’t pinch, cover eyes, restrict breathing, or trip eager paws. If your pup feels uneasy in a full suit, a festive Halloween bandana or themed leash works wonders!
Harness First: Fit costumes over or through your dog’s secure everyday harness so you never sacrifice walking control in crowded parade settings.
Pack High-Value Rewards & Water: Parades mean strange noises, crinkly capes, and lots of excitement. Keep treats on hand to reward calm focus, and give your pup space whenever they need a breather.
Know Your Dog’s Comfort Zone (It’s Okay to Leave Them Home!): Not every pup enjoys bustling crowds, loud marching bands, or seeing dogs dressed up in unfamiliar silhouettes. If your dog gets overwhelmed, anxious, or reactive in high-stimulation environments, it is perfectly okay to let them relax safely at home with a tasty chew while you head out to enjoy the parades and contests as a spectator. Being your dog’s best advocate always comes first!

Share Your Spooky Paws!

Which Halloween event are you heading to this October? What is your dog’s costume theme? Tag us in your photos @frank.endog and use #PawsitiveSpots to be featured in our seasonal stories!

Got a dog-friendly Halloween happening we missed? Submit your local spot or event here to help grow our Hudson Valley pet community!