Trick-or-Treat at the Beach, a Great Pumpkin Festival and 170 Makers on the Green: 10 Ways to Spend This Weekend Around Milford

Get the costumes out of the closet early. This weekend, kids can trick-or-treat their way down Naugatuck Avenue at Walnut Beach, Stratford throws its free Great Pumpkin Festival at Boothe Memorial Park, and the 10th Milford Artisan Market fills the Milford Green both days. It’s also the last Saturday of the season for the Downtown Milford Farmers Market.

The weather should cooperate. The National Weather Service forecast as of Thursday morning calls for a chance of showers early Saturday, then mostly sunny skies and a high near 53, with a sunny Sunday and a high near 56. Here are 10 ways to spend Oct. 17 and 18 in Milford, Stratford, Orange and West Haven.

1. Shop 170 makers at the Milford Artisan Market

The market returns to the Milford Green for its 10th year on Saturday and Sunday, Oct. 17 and 18, from 10 a.m. to 4 p.m. Admission is free. Organizer Artisan Events by Ally says about 170 local crafters and makers will be selling pottery, paintings, jewelry, woodworking, gourmet foods and more, and its website says every vendor spot for this weekend is full.

According to the organizer’s announcement, there’s a free hour of yoga at 10 a.m. both days, kids’ craft activities, food vendors, a dance exhibition and live music from Seth Adam, Elana Zabari, Sean O’Reilly and Adelaide Punkin. To mark the 10th year, the first 100 people each day get a free phone wallet and stand. It’s a good excuse to get some holiday shopping done before November. Details at artisaneventsbyally.com.

2. Trick-or-treat at Boo Fest by the Beach

The Walnut Beach Arts & Business District turns into a costume parade on Saturday, Oct. 17, from 10 a.m. to 3 p.m. Boo Fest by the Beach, presented by The Giggling Pig Milford, brings trick-or-treat stops at businesses up and down Naugatuck Avenue, live entertainment, vendors and children’s activities. Costumes are “highly encouraged,” in the district’s words. Details at walnutbeachartsandbusiness.com.

3. Bring the dog back Sunday for the Puppy Costume Contest

Dogs get their turn at Walnut Beach on Sunday, Oct. 18, at 2 p.m. The Halloween Puppy Costume Contest is free to enter with no pre-registration, and there are prizes and a “Picture your Pup” photo station. Just show up with your dog in costume. Check the district’s events page for the exact meeting spot.

4. Hit the farmers market’s final Saturday

The Downtown Milford Farmers Market wraps up its season Saturday, Oct. 17, from 8:30 a.m. to 12:30 p.m. at 108 W. Main St. The Downtown Milford Business Association’s market page lists it as running every Saturday until Oct. 17, so this is your last chance until next year. Go early, then walk over to the Green when the Artisan Market opens at 10. Details at downtownmilfordct.com.

5. Hear 43 years of local theater stories at the library

Gary and Francesca Scarpa, who founded Center Stage Theater in Shelton, will talk about Gary’s book Lessons from the Stage on Saturday, Oct. 17, from 1 to 2 p.m. at the Milford Public Library. No registration is needed. One heads-up from the library: parking behind the building is severely limited through December because of Founder’s Walk construction, so it suggests Lisman Landing, Armory Square or the River Street Garage. Details on the library calendar.

6. Take the kids to Stratford’s Great Pumpkin Festival

Stratford’s big fall tradition runs Saturday, Oct. 17, from noon to 4 p.m. at Boothe Memorial Park, 5800 Main St. Admission and parking are free. The town’s announcement lists horse-drawn carriage rides, a magic show, a costume parade and contest, a giant pumpkin carving contest, face painting and an inflatable corn maze, and the park’s historic buildings will be open. It’s also Public Safety Day, with Touch-a-Truck and safety demonstrations.

The town’s schedule: a Connecticut Dance Conservatory performance at 12:30 p.m., the magic show at 1, giant pumpkin carving judging at 2 and the costume parade and contest at 2:30. Food and activity tickets are sold at the main entrance (cash and Venmo), and ticket sales end at 3:30. Free parking is in the field next to the Boothe Memorial Railway Society, with more at Flood Middle School and free shuttles. If the weather turns, the rain date is Sunday, Oct. 18, at the same hours. Details at boothememorialpark.com.

7. Grown-ups only: Pumpkinfest at Two Roads

Roadsmary's Baby Pumpkin Fest at Two Roads

Two Roads Brewing’s 9th annual Roadsmary’s Baby Pumpkin Fest runs Saturday, Oct. 17, from 4 to 10 p.m. at 1650 Stratford Ave. in Stratford. Tickets are $20 and the event is 21 and over and entirely outdoors. The brewery’s schedule has live music from Get Lit from 4:30 to 6:30, a mummy-wrapping competition at 6:30, costume and pumpkin carving awards at 6:50 and an outdoor screening of Paranormal Activity at 7:20. Come in costume and you get a drink ticket at the door (cocktails excluded). Tickets at tworoadsbrewing.com.

8. Piano and cookies in Orange

Suzuki Music Schools opens its 2026-27 Children’s Cookie Concert series on Saturday, Oct. 17, at 3 p.m. with faculty pianist Seiji Nakanishi. The school says the concert runs about 45 minutes and is suitable for ages 4 and up, followed by a cookie reception and a masterclass with students. It’s in the library at St. Barbara Greek Orthodox Church, 480 Racebrook Road. Tickets are free (a $10 suggested donation is an option) but must be reserved. Reserve at suzukischools.org.

9. Story time with Danny the Fire Dog in West Haven

Captain Jacob Urban and Danny the Fire Dog are the special guests at the West Haven Public Library’s Family Story Time on Saturday, Oct. 17, from 10 to 11 a.m. in the Connie Sacco Room. A small craft follows. Registration is required, one child at a time, and the library says children of all ages and their caregivers are welcome. Register on the library calendar.

10. Give an old painting a spooky makeover

Also at the West Haven library on Saturday, adults can bring a thrift-store, tag-sale or attic painting to Make Your Own Masterpiece (Halloween Edition) from 2 to 4 p.m., where Katherine Tolve will help you transform it. Registration is required and the library lists 15 seats. Call (203) 937-4233 or sign up online.

Coming up next weekend

West Haven’s Halloween on the Green is Saturday, Oct. 24, at 5 p.m. on the West Haven Green, according to the city’s special events page. Details at cityofwesthaven.com.

PLAN YOUR WEEKEND

Sat., Oct. 17, 8:30 a.m.-12:30 p.m.: Downtown Milford Farmers Market (final day of the season), 108 W. Main St., Milford.

Sat., Oct. 17, 10-11 a.m.: Family Story Time with Danny the Fire Dog, West Haven Public Library. Registration required.

Sat. and Sun., Oct. 17-18, 10 a.m.-4 p.m.: 10th Milford Artisan Market, Milford Green. Free.

Sat., Oct. 17, 10 a.m.-3 p.m.: Boo Fest by the Beach, Naugatuck Avenue, Walnut Beach, Milford.

Sat., Oct. 17, noon-4 p.m.: Great Pumpkin Festival, Boothe Memorial Park, 5800 Main St., Stratford. Free admission and parking. Rain date Sun., Oct. 18.

Sat., Oct. 17, 1-2 p.m.: Gary and Francesca Scarpa, Lessons from the Stage, Milford Public Library. No registration.

Sat., Oct. 17, 2-4 p.m.: Make Your Own Masterpiece (Halloween Edition), West Haven Public Library. Registration required.

Sat., Oct. 17, 3 p.m.: Children’s Cookie Concert with Seiji Nakanishi, St. Barbara Greek Orthodox Church, 480 Racebrook Road, Orange. Free, reservation required.

Sat., Oct. 17, 4-10 p.m.: Roadsmary’s Baby Pumpkin Fest, Two Roads Brewing, 1650 Stratford Ave., Stratford. $20, 21+.

Sun., Oct. 18, 2 p.m.: Halloween Puppy Costume Contest, Walnut Beach, Milford. Free.