Dog Events in Smith Island, 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.

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!

Bring Fido for some fun indoor exercise with other pups. No reservations required, just drop in with your canine pal. Staff members will be on hand to show you how to use the agility and exercise equipment.

Dog lovers and their well-behaved canine companions are invited to explore the zoo together during this unique Halloween-themed night! Guests can stroll through select zoo areas with their dogs while enjoying new sights, smells, and interactive experiences designed to enrich both pets and zoo animals alike. The event also features themed activities and a costume contest. Participating dogs must be leashed, vaccinated, and comfortable around people and other animals.

This family- and dog-friendly evening will feature local vendors, food and treats, Halloween activities, and a costume contest with categories for pets, individuals, and groups. Bring your pup, dress up for the occasion, shop local, and enjoy a fun Halloween evening while supporting animals in the community. The Halloween Market is part of the VBSPCA’s Paws for a Cause peer-to-peer fundraising campaign, running October 26–November 6. Funds raised help support the animals in the VBSPCA’s care.

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 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.

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 with doggie trick-or-treating, treat stations and a costume contest benefiting Lucky Dog Animal Rescue. Every donation helps save at-risk dogs and cats.

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.

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.