Dog Events in Ashland, NY

This dog-friendly Halloween event features decorated trunks from local pet-friendly businesses offering treats to pups and their people. Guests can also enjoy a dog costume contest, pie-eating contest, raffles, games and more.

Every Saturday and Sunday from May through October, leashed dogs are welcome at these live outdoor performances from talented local and regional bands across a variety of genres. Enjoy cold beer and savor delicious food. Guests are encouraged to bring lawn chairs and blankets. Start and end times vary by date; see their website for schedule.

Join the Van Cortlandt Park Alliance, Van Cortlandt House Museum, and the Urban Park Rangers for a free afternoon of family and dog-friendly fun! Enjoy creepy crafts, face painting, and spine-tingling stories with LINC on the museum lawn. At 3:00 PM, don’t miss the Annual Pup Parade & Canine Costume Contest. Pups can be registered from 2:00–2:45 PM or pre-register online. Cap off the evening with a Nocturnal Creatures and Wildlife Hike led by the Urban Park Rangers from 6:00–7:30 PM.

This dog-friendly Halloween block party invites families and their pets to enjoy trick-or-treating at local businesses along a car-free Elm Street. Guests can also enjoy spooky tunes from School of Rock, show off their costumes and take part in a free afternoon of Halloween fun for all ages.

Pasta Grill Mansfield hosts a Halloween dog costume contest where pups can show off their cutest, funniest, or spookiest looks. Entry is $10 per dog, with half the proceeds benefiting the local Pet Adoption League and half going to the winner. A special menu for dogs and food and drink specials for their humans will also be available.

Don’t miss this annual event featuring a pet parade at 1 PM followed by a Halloween costume contest at 1:30 PM with prizes in categories like Best Overall, Scariest, Funniest, Cutest, Best Homemade, Best Pet & Owner Duo, Most Creative Use of Fur, and Best Barnyard Buddy. Delicious eats from food trucks and live music keep the fun going all afternoon for a paw-some autumn day! Please note that this is the only day that the farm welcomes dogs.

This dog-friendly fall festival features pumpkin picking, games, seasonal photo opportunities, a corn maze, farm attractions and fall treats. Fido must stay leashed at all times. Guests can relax around a campfire, explore the Pumpkin Pop-Up and enjoy the Glowing Pumpkin Trail.

This annual signature event of the Williamstown Holiday Walk begins with line-up and costume contest judging at 1:30 PM at the Falk Science Quad at Williams College. Dog owners are welcome to deck their hounds in festive attire for prizes in categories: Small, Medium, Large & Family Troupe. The parade will then head down Spring Street.

The Arthritis Foundation’s race is the original festive race for charity with your pup. It’s where you can strut your stuff in your favorite holiday costume. Bring a team of friends, family, and co-workers to run or walk. Please ensure your dog is kept on a leash. Check-in starts at 9 AM and the race begins at 10 AM.

Bring Fido to this fun, annual holiday event! There will be lots of activities, including the Reindog Parade on Saturday at 2 PM, old-fashioned caroling, pop-up shops, a nonprofit fair, and horse-drawn carriage rides! Merchants will be open with specials and restaurants will be ready to serve you up their best holiday cheer.

The Arthritis Foundation’s race is the original festive race for charity with your pup. It’s where you can strut your stuff in your favorite holiday costume. Bring a team of friends, family, and co-workers to run or walk. Please ensure your dog is kept on a leash. Check-in starts at 9 AM and the race begins at 10:30 AM.

On select Sundays this holiday season, bring Fido and watch him strike adorable poses with Santa! Pet Photos will be located at the Santa Set in Macy's Court. Enter through the Chipotle entrance and walk downstairs; all other entrances will be locked. Photos will be taken and available for purchase at this event. Reservations are recommended but not required.

On select Sundays, bring your furry friends, big or small, and watch them strike adorable poses with Santa. This heartwarming event is the perfect opportunity to create lasting memories and share the holiday spirit with your four-legged family members. You can find Santa in Center Court. Reservations are recommended, but aren't required.

On select Sundays this holiday season, bring Fido and watch them strike adorable poses with Santa! Pet Photos will be located on Retail Level R1 near Nordstrom. Photos will be taken and available for purchase at this event. Reservations are recommended but not required.

On select Sundays, bring your furry friends, big or small, and watch them strike adorable poses with Santa! Pet Photos will be located in Center Court. Photos will be taken and available for purchase at this event. Reservations are recommended but not required.

Experience the magic of Christmas with Fido! Visitors receive a free 4x6" photo with Santa. Other photo packages available for purchase. Advance reservations are highly recommended and can go quickly. Hours vary by store.

Experience the magic of Christmas with Fido! Visitors receive a free 4x6" photo with Santa. Other photo packages will be available for purchase. Advance reservations are highly recommended and can go quickly. Hours vary by store.

Bring Fido on the best pet-friendly scenic train rides in the country at the Santa Claus Special. Climb aboard an enclosed or open-air coach from the 1920s for a 16-mile journey through the beautiful Pennsylvania wilderness, accompanied by Saint Nick. On the 1-hour narrated train ride, you’ll learn about anthracite coal’s role in the Industrial Revolution and enjoy stunning views of the Lehigh Gorge. Well-behaved dogs are welcome to ride the train free of charge.

Experience the magic of Christmas with Fido! Visitors receive a free 4x6" photo with Santa. Other photo packages available for purchase. Advance reservations are highly recommended and can go quickly. Hours vary by store.