Dog Events in Milton, DE

Dress up your pup for a costume contest featuring prizes for the cutest, funniest, scariest, best-dressed, and pet-and-human duo costumes. Meet adoptable dogs from Grass Roots Rescue and support its mission, with 10% of event sales donated to the rescue.

Bring Fido to a party just for pups and pup-parents! Have a good time with your best furry one, and meet new friends both two- and four-legged. There will be free snacks, soft drinks, and treats from a sponsoring pet food manufacturer. Head to this double-gated dog park plenty of fun! You're welcome to BYOB.

Enroll Fido in the 1-mile walk or the 5K race! This fun-filled fall event features over 100 vendors, delicious food trucks, raffle baskets, a dog agility course, costume contests, and pup cups from a partial dog menu. And don’t forget—it’s howloween, so costumes are highly encouraged for both humans and pups. The 5K begins at 9 AM, and the one-mile walk starts at 11:00 AM.

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.

This gathering brings Newfoundland dogs and their people together at a brewery beer garden for a chance to socialize and connect with fellow Newfie lovers. Guests can choose from two meeting times, including a group stroll for the morning session. Advance registration is required, and attendees must RSVP with the number of dogs due to limited space. There will be a "Day After... Halloween" Costume Contest. Two lucky pups in costume will be chosen for some free goods!

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).

Enjoy a tail-wagging evening of Thanksgiving-themed fun featuring turkey-based dog food and treats, complimentary snacks for pet parents, and a paw-print painting station where dogs and their people can create a special holiday keepsake.

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.

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.

Stop by the Saturday after Thanksgiving with your furry friend to enjoy food, live entertainment, costume prizes, a dog zone and more! Please note that Fido isn't permitted in the ocean, and you must have a designated registrant hold your dog while you plunge.

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 8:00 AM and the race begins at 8:30 AM.

Pet Pantry of Lancaster County hosts its annual Light the Way Open House and Pet Food Drive, featuring tours of the facility, opportunities to meet staff and volunteers, free beverages and light fare, and a special display of lights honoring or remembering beloved people and pets. Visitors can donate pet food to support local families in need. Well-behaved on-leash dogs are welcome to join the event and ride the shuttle. Dogs must remain on leash at all times.

Leashed dogs are welcome at this annual holiday parade hosted by the Ridgely Lions Club, in conjunction with Christmas in Ridgely Winterfest of Lights</b! Line-up begins at 6:15 PM at the Martin Sutton Park 4th Street Parking Lot, and the parade will travel along a festively decorated Central Avenue. Santa will be at the train station after the parade for visits!

Enjoy this annual boat parade along the C&D Canal, traveling from its western entrance into Chesapeake City. Spectators can watch from scenic waterfront locations and stroll by the participating boats as they dock overnight at Chesapeake Inn and the town docks, keeping the celebration going along the canal and basin.

A community holiday parade that invites residents to bring well‑behaved, leashed dogs to watch. The city asks that all dogs be leashed and under control during the event and provides a family-friendly, community atmosphere.