Weekend Guide · Oct. 31–Nov. 1, 2026
Dog-Friendly Events Near Cheshire, CT: Weekend of Oct. 31–Nov. 1, 2026
Halloween weekend things to do with (and for) dogs near Cheshire and across Connecticut, with every event checked against the organizer’s own page.
Quick answer
Halloween weekend is a little quieter close to home, since most of the local dog costume parades happened last weekend. Nearest to us, The Animal Haven in North Haven holds a drop-in open house on Saturday afternoon. If you’re up for a drive, Castle Hill Farm in Newtown opens to dogs for its Dog Day on Sunday, with a pet parade, costume contest and corn maze. There’s also a pet costume contest in Ridgefield and adoption events in Bloomfield and Baltic, a Blessing of the Animals in Ledyard and Bark Harvest in Killingly. Every event below was checked against the organizer’s own page.
Every Friday I 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 31 and Sunday, November 1, 2026. We only list events where we could confirm the date and that dogs are welcome (or are the guests of honor) 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. One more thing: clocks fall back an hour early Sunday morning (Nov. 1), so double-check your Sunday start times.
1 event
Close to home
Open House at The Animal Haven
The Animal Haven, a North Haven shelter for cats and dogs, holds drop-in open houses most weekends, and Halloween is one of them. Staff give a tour, you can meet the adoptable animals, and they’ll answer your questions about adopting. No RSVP needed. Adoptions don’t happen at the open house itself, since they ask for an approved application first.
Dog rules: This is a visit to meet their animals. The shelter’s page doesn’t mention bringing your own pet, so please call ahead before you bring yours.
6 events
Worth the drive elsewhere in Connecticut
Dog Day at Castle Hill Farm
The one day of the year the farm opens to dogs. Enter your pup in a costume category when you check in (they take the judging photo then, so you don’t have to be there at a set time), and make a day of it with the 7-acre corn maze, hayrides to feed the cows, farm animals, pumpkins, live music and a food truck. It’s ticketed: general admission includes one dog, and each extra dog needs its own ticket.
Dog rules: Leashed at all times, and friendly with other pets, farm animals, adults and children. Clean up after your dog, including inside the maze. Dogs aren’t allowed during the farm’s regular hours, only on Dog Day.
Tickets and detailsFarm’s Dog Day pageDirections (Google Maps)
Pets on Parade Halloween pet costume contest
A free Halloween costume contest for pets. People are welcome to dress up too, but only the pets get judged, and prizes come from The Market at The Meetinghouse.
Dog Star Rescue adoption event
Dog Star’s weekly Saturday adoption event, at their new Bloomfield headquarters. You can meet adoptable dogs and learn about fostering, volunteering and donating.
Dog rules: Dog Star asks you to apply before you come to an adoption event.
Dog Star events calendarAdoption applicationDirections (Google Maps)
Blessing of the Animals
The church invites everyone, members or not, to bring their animals (real, stuffed, or photos) for a special blessing. They’re also collecting donations of food and other items for CHAIN.
Bark Harvest
The Killingly Business Association’s dog day: a dog costume contest and pet parade, an agility course, the pet photo calendar contest winner, a fun run, food and a vendor fair. All proceeds go to local pet shelters and future “Pawsitively Killingly” projects.
Dog rules: Pets must be leashed at all times.
Wings of Freedom Animal Rescue adoption event
Wings of Freedom, a foster-based dog rescue, brings adoptable pups to Everly After Floral. Chat with foster parents about their dogs or ask about fostering. Pre-approved adopters could even go home with a new best friend.
Safety first
Halloween safety tips for your dog
- Keep the candy bowl out of reach. Chocolate and anything sweetened with xylitol are dangerous for dogs. Bring your dog’s own treats if you’re out, and check the floor after the kids sort their haul.
- Give your dog a quiet room on Halloween night. A doorbell that rings all evening, plus strangers in masks, is a lot. A closed door, some music and a chew toy help, and it keeps them from slipping out while the door is open.
- Do a costume test run. Have your dog wear it 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 and move easily, and skip anything with small pieces they could chew off.
- Check the ID tag. Make sure your dog’s collar and tag are on under the costume and your contact info is current.
- Watch the decorations. Keep candles, jack-o’-lanterns, glow sticks and cords where tails and curious noses can’t reach.
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. For more ideas, see our guides to dog parks and trails in Connecticut and dog-friendly breweries.
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 Halloween 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 free new client meeting: 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 I’ll check it out for a future weekend roundup. Missed last weekend? Here’s our Oct. 24–25 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 free new client meeting. Existing clients can request visits through the client portal or app.
Get Startedor call or text 203-439-0456
