Fall Fun with Fido: Your 2025 Guide to Dog-Friendly Fall Fun in Massachusetts
- Kendra Gray, CPDT-KA
- 5 minutes ago
- 4 min read
By Kendra S. Gray, CPDT-KA
Fall in Massachusetts was made for dogs and their people. Crisp air, colorful leaves, and endless reasons to get outside – it’s the best walking weather of the year! Whether you are looking for a weekend adventure or just want to get out and soak in the season, there’s plenty of dog-friendly fall fun in Massachusetts. From Halloween parades and farm festivals to local orchards that welcome both you and your furry sidekick, we’ve rounded up some of the best events, farms, and practical tips to help you and your dog enjoy every crunchy leaf and pumpkin-spiced moment this fall.
Dog-Friendly Fall Events
There’s no shortage of howl-o-ween festivities and autumn adventures for dogs this season. Mark your calendars and grab a leash — these events are all within a reasonable drive from Holliston and the rest of the Daily Leash service area.
Sunday, October 19 – 11 am | Charlesgate Park, Boston
Dress your pup in their best costume and strut through the Farmer’s Market at Charlesgate Park. Prizes, goodie bags, and plenty of dog-themed vendors make this one a must-do for city-loving pups and their people.
Sunday, October 19 – 12 pm – 4 pm | Baramor Bar and Restaurant, Newton
This dog-friendly Halloween bash supports Last Hope K9 Rescue. Expect raffles, live music, dog treats, vendors, and costume contests. (Bonus: grown-ups get a complimentary beverage tasting.)
Sunday, October 19 – 9 am – 1 pm | Cummings School of Veterinary Medicine at Tufts University, North Grafton
Run or walk with your pup in this 5K that benefits animal welfare programs. Costumes are optional but encouraged — because nothing says fall like jogging next to a hot dog… in a hot-dog costume. Post-race activities include music, vendors, demonstrations, and more.
Saturday, October 25 – 1 pm – 2 pm | Boston Public Garden
Cash prizes, photo ops, and a Halloween pet parade through one of Boston’s prettiest and most iconic spots. Afterward, browse the Boston Open Market for pet- and seasonal-themed goodies.
Saturday, October 25 – 10 am – 2 pm | Paul Revere Heritage Site, Canton
A free event (donations benefit local rescues) with crafts, food, games, and a dog-and-human costume parade. Great small-town energy with big dog smiles.
Saturday, October 25 – 11 am – 10 pm | Park-9 Dog Bar, Everett
Everett’s dog-friendly bar turns into a spooky playground — crafts and family fun early, live music, cocktails, and a dog costume contest after dark. Cider donuts included.
Saturday & Sunday, November 1–2 | Warner Farm, Sunderland
A bit of a drive, but worth it. Mike's Maze opens its corn maze just for dogs this weekend, giving pups a rare chance to zig-zag through the fields with their humans.
Sunday, November 16 – 11 am – 4 pm | Lilac Hedge Farm, Rutland
A festive farm day with live music, food trucks, local vendors, and fall photo ops — all in support of Veterinary Technicians for Cleft Affected Animals. Cozy vibes guaranteed.
Please note: This list was compiled in October 2025. Click the links above for more information about each event, including advanced ticketing and registration.
Dog-Friendly Orchards & Farms
Apple and pumpkin season are in full swing, and several nearby farms are happy to host well-mannered dogs on leash. Here are a few favorites within about an hour of Holliston:
Hanson’s Farm (Framingham) – Pumpkin picking, sunflowers, and a corn maze.
Dowse Orchards (Sherborn) – A lovely, low-key orchard with pick-your-own apples.
Adam’s Farm (Cumberland, RI) – Pumpkin patch, hay maze, petting zoo, and a welcoming attitude toward polite pups.
Doe Orchards (Harvard) – A quiet spot with pick-your-own apples (and peaches earlier in the season).
Drew Farm (Westford) – A family-friendly orchard that allows dogs on leash.
Nashoba Valley Winery & Orchard (Bolton) – Yes, you can sip, snack, and pick apples here — with your dog in tow.
Fairmont Fruit Farm (Franklin) – A local favorite for apples and pumpkins, welcoming to leashed dogs.
Please note: This list was compiled in October 2025. Please click the links above to visit the websites or call the individual farms for more comprehensive and up-to-date information on any dog policies or restrictions.
Tips for Fall Outings with Your Dog
Before you head out on your autumn adventures, a few quick reminders to keep your outings fun and dog-friendly for everyone:
Call ahead. Farm policies can change during busy weekends or peak harvest days. Always double-check that dogs are still welcome.
Pack the essentials. Bring water, a collapsible bowl, and waste bags. Despite the cooling temperatures, it’s essential to keep your pup hydrated while out and about.
Keep them leashed and close. Farms are working properties, often with livestock, tractors, and roaming farm dogs. Keeping your dog under control and by your side is the best way to keep everyone safe.
Be the guest everyone loves. Pick up after your pup and respect off-limit areas — it helps keep these spots open to dogs in future seasons.
Go early. Crowds are lighter, parking is easier, and you and your dog will have a more relaxed experience.
Enjoy the Season Together
From Halloween parades to orchard strolls, there’s no shortage of places to enjoy the fall season with your four-legged family by your side. Whether your pup’s idea of fun is zooming through a corn maze or posing for pumpkin-patch selfies, there’s something nearby that’ll make both tails and hearts wag.