There is nothing quite like the feeling of being outside on a cool, crisp autumn day. The beautiful foliage and chill air perfectly complement the many activities and holidays that “fall” within autumn’s boundaries. Whether it’s pumpkin picking, escaping a tricky corn maze, or dressing up for Halloween, there are many fun things to do and experience this season.
Milford has a range of activities and events for people of all ages: something for everyone to enjoy. From outdoor movie nights and Halloween parades to spooky story times, here are some great ways to embrace the cooler days and nights and enjoy some frightful fun.
Boo Fest by the Beach at Walnut Beach!
On October 11th. get ready for a spooktacular day of Halloween fun for the whole family at Walnut Beach. Dress up in your best costume and join us for:
Trick-or-treat stops throughout the Walnut Beach Arts & Business District
Horse and carriage rides
Live entertainment
Vendors, children’s activities, and more!
Whether you’re here for the sweet treats, festive eats, or creative contests, there’s something for everyone. Costumes are highly encouraged!
Presented by The Walnut Beach Arts & Business Association and The Giggling Pig Milford.
The DMBA Wine Trail
The Downtown Milford Business Association is hosting its 16th Annual Wine Trail, inviting attendees to say farewell to summer with a foodie-friendly stroll through downtown, all while benefiting Junior Major League of Milford.
The Wine Trail takes place on Saturday, October 11th, from 5 p.m. to 9 p.m., in Downtown Milford. Participating boutiques and businesses open their doors and serve up pours of an assortment of wines, accompanied by tastings from Milford restaurants and eateries.
Attendees will receive a wine glass and a map of Wine Trail stops. Tickets are $50, and the proceeds benefit Junior Major League of Milford.
Tickets are a non-refundable donation to Junior Major League of Milford.
Halloween Cookie Class @ Dockside Brewery
Join Dockside Brewery for a spooktacular event on October 14th. Get into the spooky spirit with a step-by-step Halloween cookie decorating class led by NM Sweets!
In this fun, hands-on workshop, you’ll decorate 5 Halloween-themed cookies using royal icing, sprinkles, and guided techniques. This class is perfect for beginners or anyone looking to sharpen their sweet skills!
Food and Beverage must be purchased at the event. All participants must be 21 years of age or older.
Milford Artisan Market — October 18–19, 2025
The Milford Artisan Market will take place on Saturday and Sunday, October 18-19, 2025, from 10:00 am to 4:00 pm on the Milford Green at 168-176 Broad Street in downtown Milford, CT.
The Market will host over 150 local artisans selling their handmade items, including woodwork, jewelry, photography, natural products, paintings, and more. The event will also feature dance demonstrations, free one hour yoga classes, live music, food vendors and artist demonstrations. Admission is free. The event is sponsored by LeafFilter, Renewal by Andersen and Xfinity.
The event is organized by Artisan Events by Ally. Learn more at: facebook.com/milfordartisanmarket.
Junior Women’s Club of Milford presents it’s Annual Touch A Truck Event.
It’s that time of year again! The Junior Woman’s Club of Milford is excited to present its Annual Touch A Truck Event on Sunday, October 19th at Eisenhower Park from 10:00AM – 1:00 PM. This fun-filled day at Eisenhower Park is perfect for all ages.
A variety of trucks and vehicles will be on display in the lower field. Food trucks will be available for purchasing meals and drinks, and various vendors will showcase their goods and services. And most importantly, candy will be distributed at the trucks!t the trucks!
Wear a costume, bring a candy bucket/bag, and Trick or Treat around the field.
Check the website for tickets: https://82dd1e.myshopify.com/
2025 Hall-O-Weekend Festival
The Downtown Milford Business Association (DMBA) is hosting its annual Hall-O-Weekend Festival on October 24th and 25th. The festival features a variety of family-friendly, not-so-scary activities. It begins Friday, October 25th, at 6:30 p.m. with Outdoor Halloween Movie Night at the gazebo on the Green.
It continues on Saturday with several scheduled events, including:
-
- 10:00 am: Not-So-Scary Storytime with The Milford Public Library at the Gazebo.
- 11:30 am: Spooky children’s yoga with Just Be Yoga and Wellness at the Gazebo
- 12:00 pm: Costume Parade led by Milford’s Brian Smith (a.k.a Captain Kidd!)
- 10:00 am – 3:00 pm: Hay Bale Maze, face-painting, arts & crafts, vendors, and activities on the Green.
- 12:00 pm – 2:00 pm: Trick-or-treat through participating downtown businesses.
Milford Trick or Trot 5k Walk/Run
The 14th Annual Milford Trick or Trot is back for another year of fighting homelessness and hunger. The 5k benefits the Beth El Center and is a way to give back to the less fortunate in the community. Scheduled for October 25th, registration begins at 7:30 am, with the race starting at 9:00 am. The course takes runners and walkers from Lisman Landing on a scenic route through Milford Harbor and Fort Trumbull before ending back at Lisman Landing. All registrations prior to October 12th get a free t-shirt. Register at milfordtrickortrot.com. COURSE MAP– http://www.gmap-pedometer.com/?r=7622894
The Perfect Halloween Dance Party
Head to the MAC for
the Ultimate Halloween Ball with DJ Sonja on October 30th. Doors open at 7:30. DJ 8:00 – 10:30PM
- No Tricks – just Good Spirits, Batty Bats, Giddy Ghosts
- Dance as the spirits move you
- Costume Contest a sheet with sunglasses gets low marks
- Costumes not required but you have to wear something
- Speakeasy will be open. 21 and older only please
https://milfordarts.org/
Walnut Beach Halloween Parade
The annual parade is a staple that has been a fan favorite in Milford for many years. It begins at 5:00 p.m. on Halloween night (October 31st)and includes candy, costumes, a DJ, and lots of dancing. The Walnut Beach Creamery is also giving away free ice cream to anyone in a costume! At 6:00 p.m., the Walnut Beach Witches arrive to lead the Walnut Beach costume parade around the block. This is a free event that is great for kids and adults and really gets everyone in the Halloween spirit!
Walnut Beach Halloween Pet Parade
While there are many events for humans, this one is for our four-legged friends. The First Annual Walnut Beach Halloween Pet Parade will be held Saturday, October 19th, from 3:00 to 5:00 p.m. A panel of judges will decide which furry friend has the best costume, and prizes will be awarded to winners in multiple categories.
Milford Horror: Fall Movie Showings
Looking to see a good horror movie to get into the Halloween spirit? Milford Horror is the perfect place to go. The group does showings of multiple horror movies across different venues in Milford. Whether someone is a horror fan, or just wants to get into the spooky Halloween spirit, Milford Horror is the place to be.
October 3rd Watch the experimental silent horror film The Fall of the House of Usher (1928) with an original live score performed by Sea of Bones at The United Presbyterian Church of Milford. 6:30-10:00pm
October 17th Smash a City with King Kong and Godzilla! with Milford Horror at the Milford Public Library. 2:00 – 4:00 PM
For children and their families
Let out your inner giant monster at this special event that combines a screening of the 1962 classic King Kong vs. Godzilla with a chance to be a titanic monster and destroy a cardboard city. Bring your own monster suit (optional). Milford Horror is teaming up with the Milford Public Library Children’s Department to construct a city out of painted cardboard and other easily crushed materials. Before the movie, guests are invited to explore and take photos in the city. After the screening of the classic Toho monster matchup where Godzilla faces off against King Kong, guests will be invited to pretend they are the monster in a rubber suit and lay waste to the cardboard box city. Photos and slow-motion videos are encouraged!
Trick or Treat at Milford City Hall
Visitors are invited to trick-or-treat at City Hall before heading out on Halloween to collect candy and treats. City Hall will be open to trick or treaters on Thursday, October 31, from 2:00-4:30 PM.
Check back for updates!
