Dog Events in Pittsville, MD

Come dressed in your best Pups & Pals costumes to the B&O for the biggest puppy playdate of the year! Enjoy an afternoon of amazing vendors and activities under the pavilion, a train excursion to Carroll Park, a costume contest, and a “Yappy Hour” for adults. BARCS and the Maryland SPCA will also be on site. Owners must pre-register their dogs with proof of a rabies vaccine and sign a hold harmless waiver.

Bring Fido to this festive fall weekend event that welcomes leashed dogs onto the famous Boardwalk—a rare treat since pets are usually prohibited—along with their owners for two days of activities and fun. The celebration includes dog-specific vendors, photo stations, and the Humane Society of Ocean City’s announcement of “Pet of the Year,” plus a spirited Howl-O-Ween Parade where costumed pups and people march together in support of the humane society.

Bring Fido to this annual weekend event on the boardwalk! Activities for Saturday include dog-friendly vendors along the boardwalk, photo-op stations, and the Humane Society of Ocean City’s “Pet of the Year” announcement.

The Homestead Gardens Critter Crawl is a Halloween pet costume contest held during the annual Fall Festival. Dress up your pet and join the festivities while supporting the SPCA of Anne Arundel County.

Celebrate fall with Fido at this family-friendly event featuring trick-or-treat stations for kids and dogs, a harvest market, food truck, local rescue organizations, pet vendors, and festive activities throughout the afternoon. Highlights include a dog costume contest, pup parade, peanut butter eating contest, booth decorating competition, prizes, and plenty of seasonal fun for dogs and their people.

Dress up your furry friend for the costumed pet parade. Judges will be awarding prizes for creativity and charm, plus there will be door prizes and contest awards. Enjoy a scenic walk in the park with your pet, tour the historic house and blooming gardens, and discover the local wildlife that calls Hancock’s Resolution home.

Celebrate fall with a lively Halloween-themed festival featuring parades, costumes, live entertainment, and family-friendly activities. Visitors can enjoy a grand costume parade, a costumed dog parade, trick-or-treating, craft and food vendors, live music, and festive games for kids. This long-running coastal tradition draws large crowds each year and offers a fun mix of spooky creativity, community spirit, and seasonal entertainment for all ages.

A four-day arts, crafts, music and food festival on Ocean City’s south-end boardwalk. Guests can browse hundreds of handcrafted goods, enjoy free entertainment across multiple stages, and take part in interactive activities for all ages—including pet-friendly events.

This dog-friendly Halloween fundraiser invites guests to enjoy an afternoon of fun while meeting adorable, adoptable pets from the Worcester County Humane Society. Activities include a pet costume contest, silent auction and 50/50 raffle, along with food, prizes and opportunities to find a new best friend. All proceeds benefit the Humane Society and support its efforts to help animals in need.

Leashed dogs are welcome at this monthly outdoor arts market that closes West Street and Calvert Street in downtown Annapolis for local artists, live music, food, and vendors. The festival runs May through November.

A three-day festival celebrating Eastern Shore wildlife art, conservation, and outdoor traditions with exhibitions, demonstrations, and family activities across downtown Easton. Bring your well-behaved furry friends to the Bay Street Ponds, Sportsman's Pavilion, enter them in the Dock Dogs Competition, Grounds of the VFW, Beer Wetlands and Featured Yappy Hour event, and throughout downtown. Dogs aren't permitted on busses or allowed in any venue that's a community partner with (for example, the High School venue of Buy, Sell, Swap or Artifacts).

Animal lovers are invited to bring their pup and walk through the light show on foot before the show officially opens for the season. Enjoy a 2-mile route of twinkling lights and holiday music, photos with Santa, pet-friendly vendors, and more. Fido must be leashed at all times. After this event, Lights on the Bay opens as a drive-thru event through the rest of the season.

Take Fido for a stroll Thanksgiving morning with both 5-mile and 5K routes throughout the park. Register by noon on Thursday, November 13th, to ensure you get a T-shirt, and your pooch gets a cool Green Valley Turkey Trot bandana. The race begins at 9 AM.

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.

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.

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.

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.

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.

Bring Fido to this special night during Christmas in Ridgely Winterfest of Lights for a chance to visit Santa and receive a photo just in time for your holiday card. Proceeds will support the Caroline County Humane Society.

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.