Dog Events in Wintergreen, VA

This guided wine hike invites guests 21+ and their leashed dogs to explore scenic vineyard trails while enjoying curated wine tastings at stops throughout the property. The hike is moderate+ and takes approximately one hour. Hiking or tennis shoes are required. Please bring water along for you and your pup.

This dog-friendly Halloween party at the winery features wine, music and plenty of laughs, with costumes highly encouraged and a costume contest offering prizes in multiple categories. Guests can enjoy an evening of spooky fun, singing along to music and celebrating the season.

This annual festival features live bands, a diverse selection of food and drink vendors serving everything from seasonal treats to local brews. Leashed pets are welcome to join in the fun and even enter the costume contest! The event is rain or shine.

Celebrate Halloween at this all-day festival featuring costumes, candy, food trucks, vendors, live music, craft beer, and family-friendly activities. Bring your pup to enjoy the festive atmosphere, seasonal fun, and Halloween celebration with the community.

This dog-friendly Halloween celebration features a pup costume parade, photo booth, treat bar, trick-or-treating, local pet vendors and festive photo opportunities. Guests can enjoy delicious cider while their pups show off their Halloween costumes and participate in the pet food drive. Visitors can also explore seasonal activities, farm animals and pumpkin patch adventures at Great Country Farms across the way.

Explore Richmond’s Museum District with your pup during this dog-friendly walking tour. Guests and their dogs will learn about the history of this residential neighborhood, including how public art and cultural institutions have shaped the area. Dogs must be friendly with people and other dogs, up to date on vaccines, and remain leashed throughout the 1.5- to 2-mile walking tour.

Support local animal rescue at this pet-friendly community event featuring local vendors, raffles, adoptable animals, kids activities, food trucks, ice cream, and drinks from Screaming Goats Brewery. Shop for unique finds, meet pets looking for homes, and enjoy an afternoon of family fun while helping Jeepin For Paws provide care and resources for cats and kittens in need.

Well-behaved, leashed dogs are welcome to join fellow mixed-breed pups and their humans for a relaxed afternoon on the farm. Meet other dog lovers, enjoy scenic farm strolls and playful meet-and-greets, explore the Stick Library, and gather for a group photo at 2 PM.

Leashed dogs are welcome at this cozy outdoor fiber festival filled with creativity, community and fall fun! Leashed, well-behaved dogs are welcome on the first floor and throughout the outdoor spaces. Celebrate your love of knitting, crocheting, and all things fiber while shopping from local vendors offering beautiful yarns, tools, and handmade treasures. Relax with wine, beer, wine slushies and charcuterie from Vineyard Fare.

Gather with friends, family, neighbors and your pup at this cozy fall celebration featuring fire pits, comfort food, seasonal drinks, craft beer, gratitude activities, family-friendly fun, and beautiful late-fall farm views. Enjoy a relaxing day on the farm with photo opportunities, a community Thankful Wall, and plenty of space to connect before the holiday season begins.

Hosted by Bishop’s Events, this family- and pet-friendly race features a 1-mile fun run, a 5K, and a 10K. Walkers, strollers and leashed dogs are welcome to join in the festivities. Participants receive a finisher’s medal, a technical event shirt, and chip timing.

Celebrate the holiday season with Fido at this festive Christmas Tree Lighting! The event begins at 5:30 PM, with live performances leading up to the tree lighting at 6:20 PM.

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

The City of Roanoke Christmas Parade begins on Jefferson Street at Elm Avenue, turning onto Campbell Avenue, going past Market Square, and ending at Williamson Road. The parade is rain or shine and starts at 6:30 PM.

Step into a Hallmark Christmas movie as Middleburg transforms into a winter wonderland! Enjoy enchanting performances featuring carolers, dancers and actors. Dress up your pup and join the Jingle Paws Parade down Washington Street from the National Sporting Library and Museum, throughout town and end the stroll with Yappy Hour!

Celebrate the holiday season with your pup at a festive event featuring photos with Santa, holiday treats, Christmas music, cozy fire pits, family activities, warm seasonal drinks, craft beer, and holiday photo opportunities. Guests can write letters to Santa, visit the community Christmas tree, enjoy goat feeding, and create special memories on the farm.

Black Dog Salvage has invited guest vendors to set up and sell their wares for the day! Leashed dogs are invited to this fun event featuring a food, live music, art, jewelry, vintage items, plants, baked goods, wine, greenery, and more. All items for sale from guest vendors will be hand-made or upcycled. The Roanoke Valley SPCA will also be on site.

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.

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.