Dog Events in Brookeville, MD

Join the Rosslyn BID for a Halloween-themed evening of dog-friendly activities, treats and seasonal fun! There will be vendors, a beer and wine bar for pet parents, opportunity to mingle with fellow furry friends, and more. Dress your pup in their best costume for the annual dog costume contest!

Bring Fido to explore the estate’s landscaped gardens and woodlands during a special Halloween program! The event features a canine costume contest with categories including Best Homemade, Most Glamorous, Cutest, Funniest, Best Owner and Dog Combination, and Best Overall. Yappy Hour offers a signature cocktail, light snacks, and dog treats. Dogs must remain leashed, and pets aren't permitted indoors.

Dress up your pup for a festive costume parade featuring photo opportunities, voting, and prizes. Ebony’s Doggie Treats will serve as master of ceremonies. Check-in and pictures begin at 10:30 AM, followed by the parade, voting, and prizes at 11 AM.

Two- and four-legged friends are invited to celebrate Halloween in this annual event! Dress Fido in his best costume and head over for a fun-filled afternoon featuring trick-or-treating, vendors, live music, food, dog competitions, and more!

Enjoy a day filled with great food, local flavors, and community spirit at this family- and dog-friendly event. There will be a costume parade and contest for both dogs and people! Savor mouthwatering bites from Bruster's and Hardy’s BBQ, sip craft brews from Lone Oak, or enjoy Maryland-grown wines from Mazzaroth Vineyard while your pup indulges in special treats. As the evening winds down, grab a blanket and settle in for a movie screening under the stars.

On Wednesdays, during regular daytime hours, leashed dogs are welcome in the gardens (only service dogs are permitted on other days). Each adult may bring one dog. All attendees must sign an Assumption of Risk and Rules of Participation form before entering. Dogs must be leashed at all times with a non-retractable leash no longer than 6 feet. Loaner leashes are available at the Admissions Desk, and adult handlers are responsible for keeping dogs under control and out of landscape beds.

Get ready for a spooktacular evening where pups and their people can strut their stuff in the costume contest, with prizes like overnight stays, dinners, and more awarded at 7:00 PM by local celebrity judges in categories such as most creative, most adorable, funniest, and honorable mentions. Furry friends will enjoy treats, while humans sip on festive Halloween-themed cocktails and treat their pups to special Puptails. Make a night of it and book a stay on site at the Fairmont Washington DC Georgetown!

This dog-friendly farm event features Halloween trick-or-treating for pups, a chance to learn training tips from a local dog training club, and opportunities to support the Morgan Chapel Pet Food Pantry through donations. Guests can dress their dogs in costume, enjoy a day on the farm, and grab a bite from the on-site food truck. All pets must remain leashed, and owners are responsible for cleaning up after them.

Enjoy fall with a scenic run or walk through colorful garden collections, rolling hills, and streams. Seasonal activities include a Halloween costume contest, trick-or-treating, a “Thriller” dance party, and more. Dogs are welcome but must remain on a 6-foot, non-retractable leash.

This dog-friendly holiday event invites guests to explore the Winter Lights Festival on foot, choosing a leisurely 1-mile stroll or a more challenging 3-mile walk among hundreds of illuminated displays. Visitors can enjoy a hot drink and take photos with Santa while experiencing the festive lights up close. There will be no onsite sales for Walk & Wag. All tickets must be purchased online in advance. If you want to enjoy the lights from the comfort of your car, the drive-through experience, Winter Lights Festival, begins on November 28th.

You and Fido are invited to come out on Thanksgiving morning for this fun-filled charity race. Perfect for adults, teenagers, children, and even your pup, the Turkey Trot is a guaranteed way to get a healthy start to your day and do something good for your community. Be sure to register in advance by visiting the event website. Dogs who attend should be well-socialized, well-behaved, on a leash at all times and line up with their owners at the back of the pack. Please remember to clean up after your pup.

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 8 AM and the race begins at 9 AM.

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 8 AM and the race begins at 9 AM.

Enjoy a monthly dog-friendly yappy hour featuring Tito's cocktail specials, pet treats, desserts, and a welcoming social atmosphere for dog lovers. Guests can mingle with fellow pet owners, capture fun photos, and browse offerings from local vendors while supporting a good cause. A portion of proceeds from select drinks benefits the Humane Rescue Alliance.

Bring Fido to the patio for Yappy Hour every Sunday! Guests can enjoy drink and food specials, dog treats, and the chance to make some new puppy pals.

Join a gentle, all-levels yoga session surrounded by the joy of puppies and dogs. Stretch, breathe, and connect while supporting spay, neuter, and rescue programs. All friendly dogs welcome—must be up to date on vaccinations, and owners must email proof prior to the event.

Bring your pup to experience a beautiful festival of holiday lights! Scheduled dates for 2026 are November 16, 17, & 24, and December 1, 2, 28 & 29. Fido is welcome to join you on designated nights while you walk through the elegant garden trail and admire the lighted trees and displays featuring nature, winter and holiday themes. Food and beverages will be available for purchase. Tickets must be purchased online. Please check their website for all rules and regulations.

Take a 3.5-mile drive with Fido through 450 illuminated displays and holiday-lit trees! Advance ticket purchase is required for this event. Guests are invited to bring snacks and drinks to enjoy while visiting the lights. Your pup must remain in the car with your at all times. Tickets must be purchased in advance. If you want to experience the lights on foot, there will be a special dog-friendly, no-traffic night on November 23rd called Winter Lights Festival Walk & Wag.