Dog Events in Sherwood, MD

There are 6 upcoming pet friendly events within 40 kilometers of Sherwood. Use the links below to get details on each event, print directions, look at pictures, and even read reviews of last year’s event. Coming from out of town? Get a discounted rate on pet friendly hotels in Sherwood.

Pet Friendly St. Michaels Jack Russell Races
St. Michaels Jack Russell Races
Watch some of the fastest little Terriers around compete at the Jack Russell Races! This annual event brings together Jack Russell enthusiasts, dog lovers, and spectators for exciting races, food, drinks, and community fun. Dogs don't need to compete to attend, and all well-behaved pups are welcome to join the celebration. Check-in starts at 9 AM and races begin at 11 AM.
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Pet Friendly Porchfest Annapolis
Porchfest Annapolis
This community music festival transforms neighborhood porches and outdoor spaces into live performance stages, creating a walkable celebration of local music, art, and connection. Guests and leashed pups can stroll through the area enjoying performances from a variety of musicians and bands while exploring local vendors, food, and neighborhood gathering spots along the way. The rain date is October 25th.
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Pet Friendly First Sunday Arts Festival
May 3, Jun 7, Jul 5, Aug 2, Sep 6, Oct 4, Nov 1

First Sunday Arts Festival

First Sunday Arts Festival
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.
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Pet Friendly Waterfowl Festival
Waterfowl Festival
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).
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Pet Friendly Y Turkey Trot Charity 5K - Arnold Trot
Y Turkey Trot Charity 5K - Arnold Trot
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.
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Pet Friendly Lights on the Bay
Lights on the Bay
Bring Fido on this drive-through, 2-mile festive display of lights to get you into the holiday spirit. This event has become a tradition for many families! The display is a scenic drive along the shore of the Chesapeake Bay with more than 70 spectacular animated and stationary displays illuminating the roadway.
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