Main Line 2025 Dog Friendly Fall Events

Our Top Roundup of 2025 Dog Friendly Fall Events on the Main Line

When the leaves start to change and crisp autumn breezes roll across the Main Line, there’s nothing better than getting outside and enjoying the vibrant energy of the season. And if you’re a dog parent, you know fall adventures are even sweeter when shared with your pup. Fortunately, the Main Line and surrounding Philadelphia suburbs are filled with seasonal happenings that welcome four-legged family members. From food truck festivals and craft beer gatherings to bustling fall fairs and farmers markets, you’ll find plenty of opportunities to bond with your dog while soaking up the best that autumn has to offer.

We’ve rounded up some of the most exciting activities to add to your calendar. Whether you’re looking for live music, contests, pumpkin patches, or just a cozy beer garden where pups are welcome, you’ll find the perfect fit here. And for those occasions when an event isn’t quite pup-appropriate, Wagsworth Manor is always ready to provide your dog with five-star boarding and care so you can enjoy peace of mind.

Chestnut Hill Brewing Company Yappy Hour – Every Thursday

If your ideal fall evening includes craft beer, wood-fired pizza, vegan bites, and dogs wagging happily by your side, then Chestnut Hill Brewing Company’s weekly Yappy Hour belongs on your calendar. Located in Chestnut Hill, this brewery is known for its relaxed, family-friendly, and dog-friendly atmosphere. Both indoor and outdoor seating are available, making it an all-weather option for gathering with friends, family, and of course, your pup.

Every Thursday from 4:00 to 6:00 p.m., the beer garden transforms into a canine celebration. During Yappy Hour, your pup can indulge in a $1 Pup Cup, or if you really want to spoil them, spring for the $5 Pup Cup Flight. Even better, when you spend $50 or more, you’ll receive a free dog leash – perfect for future brewery outings or strolls along the Wissahickon trails.

For those looking to kick off the weekend a little early, Yappy Hour offers the perfect mix of food, fun, and furry friends. This weekly gathering is one of the most reliable Dog Friendly Fall Events on the Main Line, giving you a reason to look forward to Thursdays all season long.

Skippack Food Truck Festival – September 6th

Food trucks and dogs – what could be better? The Skippack Food Truck Festival, taking place on Saturday, September 6, 2025, brings together some of the best mobile kitchens in the region for an afternoon of culinary adventure. The charming streets of Skippack Village, located near Basta Pasta, come alive with aromas of savory entrees, sweet desserts, and everything in between.

This festival is designed for the whole family, dogs included. Bring your pup along for a leisurely stroll through the bustling rows of trucks and vendors. While you enjoy tacos, barbecue, or international bites, your furry friend can take in the sights, sounds, and smells of this lively event. Don’t forget to pack a picnic blanket and perhaps a few extra treats for your pup – you’ll want to settle in and stay awhile.

Annual Radnor Fall Festival – Sunday, September 24th

The Radnor Fall Festival is one of the highlights of the Main Line’s autumn calendar, and 2025 promises another unforgettable day of community spirit, live entertainment, and dog-friendly fun. On Sunday, September 24th, North Wayne Avenue transforms into a lively hub of activities for the entire family.

Children will love the rides and activities scattered throughout the festival, while adults can browse an impressive lineup of local vendors offering everything from handmade crafts to small business services. Community organizations are also out in force, sharing their work and encouraging neighbors to get involved in meaningful causes.

But the real showstopper for dog lovers is the annual Top Dog Contest. Pups of all shapes, sizes, and personalities strut their stuff before an adoring audience. Whether your dog is a natural performer or simply loves the spotlight, the Top Dog Contest is a joyful celebration of the bond we share with our pets. Even if you’re not entering, cheering for your favorite contenders is an experience you won’t soon forget.

As one of the largest Dog Friendly Fall Events on the Main Line, the Radnor Fall Festival is a can’t-miss opportunity for families and dog parents alike. Bring your pup, your appetite, and your community spirit for a day that captures the very best of autumn.

Dog Day at the Lansdowne Farmers Market – October 4th

Farmers markets are already a treat for the senses, but when they dedicate a day to dogs, it becomes truly special. On Saturday, October 4th, the Lansdowne Farmers Market will host Dog Day, a celebration of all things canine. Running from 9:00 a.m. to 1:00 p.m. at The Landing (30 N. Lansdowne Ave), this event promises fun, food, and festivities for both humans and their four-legged companions.

Highlights of Dog Day include fun contests where pups can show off their unique talents or looks, with bragging rights (and maybe prizes) going to the winners. Vendors specializing in pet treats and accessories will be on hand, making it the perfect time to spoil your furry friend. And of course, the farmers market itself will be stocked with fresh produce, baked goods, and local delicacies for you to enjoy.

Photo opportunities abound, so don’t forget to capture those heartwarming moments with your pup. This is the kind of event that turns into a cherished memory – standing among neighbors, fresh flowers in hand, with your dog wagging happily by your side.

Upper Merion Community Fair and Fall Festival – October 4th

The first Saturday of October brings with it another standout event: Upper Merion Township’s Community Fair and Fall Festival. Taking place at Heuser Park starting at 12:00 p.m., this festival offers a little bit of everything – live music, crafters, community organizations, food vendors, and more.

Kids will love the hayrides, pumpkin patch, and inflatable attractions. Adults can browse the many booths featuring local businesses, artisans, and nonprofits. And for dogs? A dedicated doggy play area with kiddie pools provides a refreshing way for pups to stay cool while enjoying the excitement of the day.

This festival is free to the public and explicitly welcomes pets, making it one of the most accessible Dog Friendly Fall Events in the region. Just be sure your pup is leashed and well-behaved, as festival organizers are committed to ensuring a safe and welcoming environment for all attendees.

Dog Friendly Faire Days – October 2025

Step back in time with your pup at the Pennsylvania Renaissance Faire during Dog Friendly Faire Days in October. This unique event welcomes friendly, well-behaved dogs to enjoy all the revelry of the Faire alongside their human companions. To participate, owners must complete a few simple steps in advance: submit the Qualified Dog Registration Form, waiver, and a photo of their pup, along with vaccine expiration details. Once approved, you’ll receive an email with a link to purchase a date-specific “Royal Hound Ticket” for $7.50 per dog. Tickets must be presented – either printed or on your phone – for each visit, and they are valid only for the dog registered. While it takes a little preparation, the payoff is worth it: the chance to stroll through costumed villages, enjoy live entertainment, and experience the Renaissance magic with your best friend by your side. With its careful policies in place, Dog Friendly Faire Days remains one of the most memorable and well-structured Dog Friendly Fall Events in Pennsylvania.

Beyond Dog Friendly Fall Events – Make Boarding Fun and Memorable For Your Pup

As you fill your calendar with these incredible Dog Friendly Fall Events, remember that not every outing will be dog-friendly. For those occasions, Wagsworth Manor is here to provide the highest level of care, boarding, and attention your pup deserves. With luxurious accommodations and a dedicated staff, we make sure your dog feels loved and secure while you enjoy your event worry-free.

Reach out to Wagsworth Manor today to learn more about boarding options and ensure your pup has a fall to remember – whether they’re by your side at a festival or enjoying their own special retreat.