MILFORD — Mark the calendar: Santa, the carolers and the horse-drawn carriages are coming back to downtown Milford. The Downtown Milford Business Association (DMBA) has posted its 2026 holiday lineup, with three free shop-local events running from Thanksgiving weekend to the week before Christmas.
Here’s the short version: Small Business Saturday on Nov. 28, the 24th annual Lamplight Stroll on Friday, Dec. 4, and Sip & Shop on Thursday, Dec. 17. All three are free to attend. The two Green events are outdoors only this year, according to the DMBA.
Small Business Saturday: Saturday, Nov. 28, 10 a.m. to 3 p.m.
The weekend after Thanksgiving, the Milford Green at 84 S. Broad St. fills with tents for the DMBA’s take on Small Business Saturday, the nationwide shop-small day American Express started in 2010.
The association says to expect 60-plus vendors, including food trucks and food vendors, plus 10-plus downtown storefronts taking part: restaurants, spas, bookstores and more. Vendors will have arts and crafts, clothing, jewelry, home décor and other gifts.
There’s a giveaway, too. The first 250 shoppers to complete the Small Biz Saturday Punch Card get a free “Shop Local Milford” tote bag with exclusive deals from DMBA members. The DMBA says details on how to take part are coming soon.
Lamplight Stroll: Friday, Dec. 4, 5 to 9 p.m.
This is the big one. The DMBA calls the 24th Annual Lamplight Stroll “an evening straight out of a Christmas story,” and the list backs that up: carolers singing classics around downtown, horse-drawn carriage rides, Santa and his elves taking wish lists and posing for photos, and a bonfire on the Green with hot chocolate.
The Stroll spreads across the Milford Green and downtown storefronts, with 60-plus vendors and food trucks and 10-plus storefronts.
Kids (and competitive grown-ups) can pick up a printable Stroll Passport at the DMBA tent on the Green. Collect stamps at 20-plus participating vendors around downtown and the Green for a chance at holiday prizes, which the DMBA says include a TV.
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Sip & Shop: Thursday, Dec. 17, 5 to 8 p.m.
Still have names left on the list a week before Christmas? The DMBA pitches Sip & Shop as a holiday shopping night out with friends: festive drinks while you browse participating downtown boutiques for clothing, jewelry, home décor, kitchen goods, books, pottery, cosmetics, kids’ clothes and more.
The association lists more than 10 participating storefronts. Named so far:
- Sunshine Ceramics
- Bond & Co
- Make Up, Make Up
- Whispers
- Inside Living
- Mind, Body & Wellness
Where to park
The DMBA lists free parking for its holiday events at:
- Harborside Middle School, 175 High St.
- The new public parking under 44 River St.
- Armory Square/Harborwalk, 22 Broad St.
- Lisman Landing, 37 Helwig St.
- The Senior Center, 9 Jepson Dr.
- Along Broad Street near the Green
- Wasson Field, 108 W. Main St.
- Parsons Government Center, 70 W. River St.
One tip: Milford Public Library has warned that parking behind its building is limited through December because of Founders’ Walk construction, so the lots above are your best bet.
Want to be a vendor?
Vendor and sponsorship applications for the events are open on the DMBA’s website, downtownmilfordct.com, which also has the full event details.
DOWNTOWN MILFORD HOLIDAY DATES
Sat., Nov. 28: Small Business Saturday, 10 a.m.–3 p.m., Milford Green, 84 S. Broad St.
Fri., Dec. 4: 24th Annual Lamplight Stroll, 5–9 p.m., Milford Green and downtown storefronts
Thu., Dec. 17: Sip & Shop, 5–8 p.m., participating downtown storefronts
Cost: Free to attend
Info: downtownmilfordct.com/events
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