Dog Events in Chestertown, MD

Here are the pet friendly events closest to Chestertown. Use the links below to get details on each event, print directions, look at pictures, and even read reviews of last year’s event.

Pet Friendly Tail Waggin' Wednesday with the Trenton Thunder
Tail Waggin' Wednesday with the Trenton Thunder This summer, the ballpark is going to the dogs! Well-behaved pups will be permitted to join you on select Wednesday games presented by NutriSource Pet Foods. Fido doesn't need a special ticket, though purchasing an extra seat is recommended for more space. Pets aren't permitted in the Luxury Suite Level and must remain leashed at all times. Designated relief areas are provided outside the gates, with cleanup supplies available inside. Water stations and vendor tables are also set up throughout the concourse for dogs and their owners to enjoy during the game. See Details
Pet Friendly Run for the Paws 5K & 1M Dog Walk
Run for the Paws 5K & 1M Dog Walk A charity race and fun dog walk that raises funds for Humane Animal Partners while bringing the community and their pets together for a morning run/walk. The event includes a timed 5K, a 5K walk division, and a 1-mile dog walk. See Details
Dirty Habit Presents: Paws and Palms Join a sun-soaked courtyard gathering at the Kimpton Hotel Monaco Washington DC, with laid-back island vibes, cocktails, and four-legged companions. Guests can enjoy specialty treats, pup cups, light music, photo ops, and a relaxed tropical atmosphere designed for lingering and socializing. See Details
Peach Festival at Peddler's Village Celebrate peach season with Fido at this family-friendly festival featuring peach-themed treats, live entertainment, shopping, and seasonal food and drinks. Guests can stroll through the Village with leashed pups, browse local shops, enjoy live music, and sample peach-inspired specialties throughout the weekend. See Details
Daisy’s Legacy Anniversary Celebration Celebrate two years of rescue, love, and community with an evening of pizza, pups, and good vibes. Enjoy an all-you-can-eat buffet, music, raffle prizes, and a photo booth on a pet-friendly patio. Rescue pups will be on-site, and donations of dog items are welcome to support future furry friends. Well-behaved, leashed dogs are welcome. See Details
Seafarers & Maritime Celebration at Historic Cold Spring Village Bring your furry friend to this event featuring pirates, music and family fun! Guests will learn about maritime history and culture of the Jersey Cape. Historically-clothed interpreters will demonstrate the trades, crafts and lifestyles of Early America. Dogs must be leashed at all times. Please ensure dogs are leashed and picked up after, and note that dogs aren't permitted inside buildings. See Details
Bark at the Park with the Trenton Thunder Bring out your pup for Bark at the Park presented by Dogs & Cats Rule! One lucky fan and their dog could win $10,000! Fido doesn't need a special ticket, though purchasing an extra seat is recommended for more space. Pets aren't permitted in the Luxury Suite Level and must remain leashed at all times. Designated relief areas are provided outside the gates, with cleanup supplies available inside. Water stations and vendor tables are also set up throughout the concourse for dogs and their owners to enjoy during the game. See Details
Woof Wednesdays with the Aberdeen IronBirds Bring Fido out to the ballgame on select Wednesdays throughout the season. Check the website's schedule to catch a dog-friendly baseball game! Special accommodations and activities are often available for canine guests. It's a perfect opportunity to enjoy America's pastime with your four-legged family members. See Details
Yappy Hour at The Stacks Bring Fido out for an evening of socializing, games, and community fun! Guests can enjoy music from a live DJ, cocktails and mocktails, snacks, cornhole, giveaways, and other activities while dogs make new furry friends. Open to residents and non-residents. The event will take place in the park area at Dry Dock Park (located on1st street outside the Colette lobby). See Details
Summer Renaissance Festival at Shipgarten Step into a whimsical, medieval world at this outdoor celebration of old-world charm with live entertainment, lively music, and interactive games. Feast on hearty festival fare, sip ale, mead, and themed drinks, and strike your best pose for royal photo ops. Don your crown, tunic, or corset and compete in the costume contest. There's an off-leash area for Fido, and pup cups! See Details
Wags & Whiskey at Sagamore Spirit Distillery Raise a glass with your pup at this fun fundraiser benefiting Baltimore Animal Rescue and Care Shelter (BARCS). Enjoy live music, craft cocktails, food trucks, and a special giveaway for dogs, with fundraiser passes including two cocktail tickets and a $10 donation to BARCS. Dogs are welcome but must remain leashed, and guests 21 and older must present valid ID to drink on campus. See Details
Bark in the Park with the Fredericksburg Nationals Bring your favorite four-legged FredNats fan to the ballpark! All dogs are welcome to enjoy the game with their owners. This event is presented by St. Francis Animal Hospital and will take place on the following dates: May 13, June 3, June 17, June 24, July 22, August 5 and August 19. See Details
Dog Days of Summer Grab your leash and take a stroll with Fido through downtown Skippack while local shops greet your pooch with water bowls and snacks. Spoil your pet with a variety of delicious treats and browse pup pop-ups offering unique pet products and services. See Details
SPCA of Anne Arundel County’s Puppy Plunge Bring your family, friends and leashed pups to the best beach bash in Anne Arundel County! There will be live music, food and drinks for purchase, vendors, fun contests and activities, beach access for dogs to splash and play, and more. See Details
Long’s Park Amphitheater Summer Music Series The summer schedule features a different performance each Sunday from early June until late August. Bring your lawn chairs and set up on the grass beside your leashed dog for an entertaining evening! Check their website for this year's lineup. See Details
Select dates May 1–Aug 25

Wag Your Tail Tuesdays

Wag Your Tail Tuesdays Bring Fido to the Bark in the Park, where he can enjoy the day for free with a donation to a local animal shelter. Acceptable donations include paper towels, treats, food and toys. This special event takes place at home on Tuesdays on the following dates: May 26, June 16, June 30, July 7, July 28 and August 11. There's also a Friday event on May 1 that welcomes pups. See Details
Summer Nights at Hagley Guests are invited to bring their dogs for a scenic walk along Brandywine's picturesque mile. Picnic or enjoy Dogfish Head craft beer and Woodside Farm Creamery ice cream. Please keep leashes manageable for passing bicyclists, and remember to bring water and waste bags for your pup. This event is weather-dependent. See Details
Pup Stroll Wednesdays at Meadowlark Botanical Gardens 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. See Details
Bring Your Dog to the Game with the Reading Fightin Phils Bring Fido out to watch a Fightin Phils baseball game! Dog-friendly games are held on select dates throughout the season, so make sure to check the website's schedule to catch a game. Water stations will be available multiple areas, as well as a separate space for pets to do their business. See Details
Woof Wednesdays with Chesapeake Baysox Leashed and vaccinated dogs are welcome to enjoy Bark in the Park! Please present current, valid vaccination tags at the gate before entering. The event will take place on the following dates: April 8, April 22, May 20, June 3, June 17, June 24, July 22, August 5, August 19 and September 2. See Details
Chestertown, MD, US