Weekend Guide · Oct. 24–25, 2026
Dog-Friendly Events Near Cheshire, CT: Weekend of Oct. 24–25, 2026
Dog-friendly things to do around Cheshire and across Connecticut this Saturday and Sunday, with every event checked against the organizer’s own page.
Quick answer
Halloween weekend is here, and dogs are invited. Closest to home, Cheshire’s Great PUPkin dog costume parade is Sunday afternoon on the St. Peter’s lawn on Main Street, and Armada Brewing in New Haven hosts Puppy Halloween the same afternoon. Two Roads in Stratford holds its rescheduled Paws & Pints dog day on Saturday. Farther afield, there are dog costume parties in Manchester, Greenwich, New London and Groton, plus a group dog walk in South Windsor. Every event below was checked against the organizer’s own page.
Every Friday we round up dog-friendly things to do around Cheshire, Southington, Wallingford, Hamden, North Haven, Meriden and New Haven. Here’s what’s happening this weekend, Saturday, October 24 and Sunday, October 25, 2026. We only list events where we could confirm the date and that dogs are welcome on the organizer’s own page or an official listing.
Before you go: plans can change with the weather. Please check each organizer’s page or social media the morning of the event, and bring water, waste bags and a sturdy (non-retractable) leash.
3 events
Close to home
The Great PUPkin dog costume parade at Homemade Halloween
Ball & Socket Arts brings its Homemade Halloween to Cheshire’s Community Pumpkin Patch at St. Peter’s: a homemade dog costume contest and parade, plus a jack-o’-lantern design contest. Canine contestants register at 1:30 PM, and the winning pup takes home a gift basket. Not entering? You’re welcome to come cheer on the parade.
Dog rules: Bring your pup in a homemade costume. Keep your dog leashed and comfortable around a crowd.
St. Peter’s event pageBall & Socket Arts event detailsDirections (Google Maps)
Puppy Halloween at Armada Brewing
A costume party for dogs on the New Haven waterfront, with treats for the dogs and prizes for the winners. Professional photos of your pup are available for $10, and photo proceeds benefit Where the Love Is Animal Rescue.
Dog rules: Costumed pups welcome. Guests who order drinks must be 21+.
Paws & Pints at Two Roads Brewing (rescheduled date)
A free, family-friendly dog day co-hosted with Dog Friendly Finds CT: pet vendors, foster information from New England Puppy Rescue, lighthearted dog competitions like Musical Sit, free pup caricatures and a Dog Play Zone with a timed doggie drag strip ($10 or $20 for the play zone). No ticket needed.
Dog rules: Dogs must be leashed at all times. No retractable leashes at this event. Please clean up after your dog.
5 events
Worth the drive elsewhere in Connecticut
Howl-O-Ween at Elicit Brewing
A dog-friendly Halloween party with a pup costume contest, prizes and dog-themed vendors. A portion of event proceeds benefits Dog Star Rescue, which will also have adoptable dogs on hand to meet.
Dog rules: Per Elicit’s Manchester FAQ, dogs are welcome on the patio only (not inside), and must be leashed and well-behaved.
Elicit Howl-O-Ween pageElicit Manchester eventsElicit Manchester FAQ (dog policy)Directions (Google Maps)
Team Dog Star group dog walk and costume contest
Dog Star Rescue’s group walk on a 2.7-mile loop, with a prize for the best dog costume. You don’t need to have adopted from Dog Star to join. They ask walkers to sign up ahead so they can plan, and they’ll adjust if the weather is bad.
Dog rules: Your dog must be fully vaccinated and very dog-friendly.
Howl & Prowl Costume Party in the Park
The 18th annual Howl & Prowl, presented by Pet Pantry Warehouse, with pet costume contests, pet vendors, food trucks, music and treats. All proceeds benefit Adopt-A-Dog.
Dog rules: Costume contest sign-up is on the event page.
Howl-o-ween on Bank
A first-year dog-friendly Halloween party and dog costume contest from Barks & Recreation, with local vendors, a photo booth and a “Bark Street” stamp passport for visiting participating Bank Street businesses.
Dog rules: Dogs should be comfortable at a public event around other dogs and people, and must stay leashed and supervised by an adult.
Greater Mystic Chamber event listingDirections (Google Maps)
Howl-O-Ween pet costume party
Cubby’s Crusade, a special needs animal rescue, and Pet Supplies Plus host a Halloween pet costume party with prizes, a photo op, bobbing for frisbees and trick-or-treat bags for dogs. Costumes encouraged.
Event page (Eventbrite, posted by Cubby’s Crusade)Directions (Google Maps)
Safety first
Costume-day tips for your dog
- Do a test run. Have your dog wear the costume at home for a few minutes first. If they freeze, scratch at it or try to pull it off, a festive bandana is just as cute.
- Keep it comfortable. Make sure your dog can see, hear, breathe, bark and go to the bathroom easily. Skip anything with small pieces they could chew off.
- Watch the treats. Halloween candy, especially chocolate and anything with xylitol, is dangerous for dogs. Bring your dog’s own treats.
- Read your dog. Crowds, costumes and other dogs can be a lot. If your pup seems stressed, take a break somewhere quiet or call it a day.
- Check the ID tag. Make sure your dog’s collar and tag are on under the costume and your contact info is current.
Evergreen spots
Not into crowds? Dog-friendly ideas this weekend
These aren’t events, just reliable, dog-friendly places close to home for a fall walk.
Farmington Canal Heritage Trail
A multi-use rail trail through town. The trail organization asks users to keep pets leashed and close.
Sleeping Giant State Park
CT DEEP lists pets as allowed on leash in the picnic areas and on the hiking trails.
While you’re out
Out for the day? We’ve got the dog covered
If your weekend plans don’t include the dog, our team offers dog walks, pet sitting visits and overnight care in Cheshire, Southington, Wallingford, Hamden, North Haven, Meriden and New Haven. New clients start with a meet & greet: you’ll meet with a member of our team before your first service. Rates are on our Services & Pricing page.
Know of a dog-friendly event coming up near Cheshire? Let us know and we’ll check it out for a future weekend roundup.
Need a dog walker or pet sitter?
Tell us about your pets and the care you’re looking for, and our office will reach out to set up your meet & greet. Existing clients can request visits through the client portal or app.
Get Startedor call or text 203-439-0456
