Downtown Milford’s big grown-up night of the fall lands this Saturday. The Downtown Milford Business Association’s 17th annual Wine Trail sends ticket holders from shop to shop with a commemorative glass on Saturday, Oct. 10, and it’s only one piece of a full Columbus Day weekend.
There’s also a 10-hour music festival on the river at Stonebridge, a free dog party at Two Roads in Stratford, West Haven’s Italian Heritage Celebration and a Sunday collectibles show in Orange. Here are nine ways to fill Friday, Oct. 9, through Sunday, Oct. 11. Every date, time and price below comes from the organizer’s own page.
1. The Downtown Milford Wine Trail (Saturday, Milford)
The DMBA calls the Wine Trail “the unofficial kickoff to the fall season in Downtown Milford.” Participating boutiques and businesses open their doors and pour wine, paired with tastings from Milford restaurants and eateries. Every ticket holder gets a wine glass and a map of the stops.
Why go: It’s a walkable night out downtown with food and wine at every stop, and the money stays in town. Ticket proceeds are a nonrefundable donation to the Junior Major League of Milford, the city’s youth baseball league.
When: Saturday, Oct. 10, 5 to 9 p.m.
Where: Check in at the DMBA booth in front of Milford Bank, 33 Broad St. Registration starts at 5 p.m.
Cost: $55, bought in advance
Tickets: downtownmilfordct.com
The DMBA hasn’t posted the list of participating businesses yet, so the map you get at check-in is your guide.
2. Fall Fest at Stonebridge (Saturday, Milford)
If you’d rather have live music than a wine glass, Stonebridge on Daniel Street hosts the 6th annual Fall Fest on Saturday. It benefits the Norma Pfriem Breast Center, which has locations in Fairfield, Trumbull and Bridgeport. Organizers also say every dollar collected at the door this year goes to Darik Pearson, to help him in his fight against cancer.
The festival site lists Shot Down on the main stage, plus an acoustic stage, and says more of the lineup is still “coming together.”
When: Saturday, Oct. 10, noon to 10 p.m. (per the Pink Pledge event listing)
Where: Stonebridge, 50 Daniel St., Milford
Cost: $15 in advance, $20 at the door
Details: ctfallfest.com
Both the Wine Trail and Fall Fest are downtown, so it’s easy to do some of each.
3. Downtown Milford Farmers Market (Saturday morning, Milford)
Start Saturday early at Wasson Field. The DMBA has run the Downtown Milford Farmers Market since 2005, and the association says nearly 800 people come through each week. Its market page lists Saturdays through Oct. 17, so you’ve got this weekend and one more.
When: Saturday, Oct. 10, 8:30 a.m. to 12:30 p.m.
Where: Wasson Field, 108 W. Main St., Milford
Cost: No admission; pay vendors for what you buy
Details: downtownmilfordct.com/farmers-market
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4. Paws and Pints at Two Roads (Sunday, Stratford)
Bring the dog. Two Roads Brewing and Dog Friendly Finds CT are hosting a fall edition of Paws & Pints, a free, family-friendly and dog-friendly afternoon in the brewery’s Hop Yard. The brewery lists pet vendors, acoustic music from local duo Round Two, lighthearted dog contests like Musical Sit, and free caricatures of you and your pup from noon to 3 p.m. New England Puppy Rescue will be there with information on fostering.
Alpha Dog Events is bringing a Dog Play Zone with a timed “Doggie Drag Strip”: $10 for two minutes or $20 for five. The Parlor pizza truck will be on site, and Two Roads says it will donate $1 from every pint sold during the event to the Stratford Animal Rescue Society. Dogs must be leashed, and retractable leashes aren’t allowed.
When: Sunday, Oct. 11, noon to 4 p.m.
Where: Two Roads Brewing, 1650 Stratford Ave., Stratford
Cost: Free, no ticket needed (the drag strip and food and drinks cost extra)
Details: tworoadsbrewing.com
5. A free Hop Yard concert with Tin Sandwich (Saturday, Stratford)
The day before, Two Roads’ free Hop Yard Concert Series brings in Tin Sandwich, a band that mixes Southern rock, blues and harmonica-driven jams. Kids are welcome, dogs are welcome in the Hop Yard, and the brewery says to bring lawn chairs.
When: Saturday, Oct. 10, 4 to 6 p.m.
Where: Two Roads Hop Yard, 1650 Stratford Ave., Stratford
Cost: Free
Details: tworoadsbrewing.com
6. Italian Heritage Celebration (Friday, West Haven)
West Haven’s 27th annual Italian Heritage Celebration honors Paul M. Frosolone, longtime president of the West Haven Italian American Civic Association, as the city’s 2026 Italian American of the Year. According to the city, Mayor Dorinda Borer and members of the Italian Heritage Committee and the civic association will escort him to the front steps of City Hall to Italian music. Liz Levy will sing the U.S. and Italian national anthems before an Italian blessing.
When: Friday, Oct. 9, at noon
Where: Front steps of City Hall, 355 Main St., West Haven
Cost: Free
Details: City of West Haven special events
7. Last Saturday for the Tony Inzero Farmers Market (Saturday, West Haven)
West Haven’s city-run farmers market, going since 2000, wraps up its season Saturday. The city’s schedule runs from July 9 to Oct. 10, with Connecticut farmers selling homegrown fruits and vegetables and crafters selling homemade goods next to the Oak Street Beach boardwalk.
When: Saturday, Oct. 10, 10 a.m. to 3 p.m.
Where: Next to the Oak Street Beach lot, off Captain Thomas Boulevard, West Haven. The city lists parking in the Oak Street municipal lot and on Palace Street.
Cost: Free to browse
Details: City of West Haven farmers market
8. Coins, cards and comics at the Orange collectibles show (Sunday, Orange)
Got a coin jar or a box of old baseball cards? The Collectible Show, Coins & Sports Cards at American Legion Post 127 lists U.S. and world coins and sets, comics, cards, memorabilia, vintage cards, wax boxes, autographs and supplies.
When: Sunday, Oct. 11, 9 a.m. to 2 p.m.
Where: American Legion Post 127, 630 Grassy Hill Road, Orange
Cost: $2
Contact: Fred and Karen Riso, 203-265-1813
Details: show listing
9. Halloween candy taste tests for kids (Saturday, Orange)
Case Memorial Library is letting kids taste-test Halloween candy, vote and “crown the ultimate winner.” There are two sessions: tweens in grades 4 to 6 from noon to 1 p.m., and teens in grades 7 to 12 from 3 to 4 p.m.
When: Saturday, Oct. 10
Where: Case Memorial Library meeting room, 176 Tyler City Road, Orange
Cost: No fee listed; registration required. Tell the library about any food allergies when you sign up.
Details: Case Memorial Library calendar
Heads-up: Sleepy Hollow is sold out this weekend
Pantochino’s The Real Housewives of Sleepy Hollow opens Friday at the Milford Arts Council, 40 Railroad Ave., but all three opening-weekend shows are marked sold out on Pantochino’s ticket page. Later performances run through Oct. 30. Details at pantochino.com.
PLAN YOUR WEEKEND
Fri., Oct. 9, noon: Italian Heritage Celebration, West Haven City Hall, 355 Main St. Free.
Sat., Oct. 10, 8:30 a.m.-12:30 p.m.: Downtown Milford Farmers Market, Wasson Field, 108 W. Main St., Milford. No admission.
Sat., Oct. 10, 10 a.m.-3 p.m.: Tony Inzero Farmers Market (season finale), by the Oak Street Beach lot, West Haven. Free.
Sat., Oct. 10, noon-1 p.m. and 3-4 p.m.: Halloween candy taste tests (grades 4-6, then 7-12), Case Memorial Library, 176 Tyler City Road, Orange. Registration required.
Sat., Oct. 10, noon-10 p.m.: Fall Fest at Stonebridge, 50 Daniel St., Milford. $15 advance, $20 door.
Sat., Oct. 10, 4-6 p.m.: Tin Sandwich, Two Roads Hop Yard, 1650 Stratford Ave., Stratford. Free.
Sat., Oct. 10, 5-9 p.m.: 17th annual Downtown Milford Wine Trail. Check in at Milford Bank, 33 Broad St. $55 in advance.
Sun., Oct. 11, 9 a.m.-2 p.m.: Collectible Show, Coins & Sports Cards, American Legion Post 127, 630 Grassy Hill Road, Orange. $2.
Sun., Oct. 11, noon-4 p.m.: Paws & Pints, Two Roads Brewing, 1650 Stratford Ave., Stratford. Free.
Which stop is first on your weekend list?
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