The Milford Turkey Trot grew from 607 people in 2021 to 1,925 in 2025 without closing a single Milford street. Its loop past Gulf Beach is all on sidewalks. Two days later, the Downtown Milford Business Association's Small Business Saturday follows the same pattern. This year it leaves the library behind and puts the whole market outside on the Milford Green.
So Thanksgiving weekend 2026 in Milford happens on public ground the city already has. That shapes the practical details: when to pick up your bib, which cans to bring, where to park on Saturday, and why some of the drop-off spots for the food drive are places you already know.
Thursday, 9 a.m.: a route with no barricades
The 6th annual Milford Turkey Trot starts Thanksgiving morning, November 26, at 9 a.m. at Fowler Pavilion, 1 Shipyard Lane, behind the library. The organizers call it a fun run and walk for charity, not a race. No roads will be closed, and everyone is expected to stay on the sidewalks and follow street laws. Because of that, the event welcomes kids, strollers and pets on leashes.
The full loop is a little over 3 miles and covers the shoreline side of town:
- Head out from Fowler Pavilion up Shipyard Lane.
- Turn south on Gulf Street and follow it all the way past Gulf Beach.
- Turn left at Calf Pen Meadow and head northwest on Buckingham Avenue.
- Near Jimmy's Apizza, head west on New Haven Avenue.
- Rejoin Gulf Street and finish back down Shipyard Lane.
There are also two shorter out-and-back options toward Gulf Beach. One is 1 mile total, and the 2-mile option goes all the way to the beach and back. Both have sidewalks the whole way. If you'll be out of town, you can register as a virtual participant and still support the charities.
The numbers behind a no-closure event
The Trot is run entirely by volunteers, and the organizers say no one is paid for their work or time. Here is how it has grown, by the organizers' own count:
| Year | Trotters | Raised for charity |
|---|---|---|
| 2021 | 607 | $8,000 |
| 2022 | 857 | $20,000 |
| 2023 | 1,460 | $38,000 |
| 2024 | 1,881 | $45,000 |
| 2025 | 1,925 | $48,000 |
In those five years, turnout more than tripled and the amount raised grew six-fold. The running total stands at $159,000. The biggest jump came between 2022 and 2023, when turnout rose by about 600 people. Another 421 people joined in 2024, and growth slowed to 44 more people in 2025. With almost 2,000 people on the sidewalks of Gulf Street and Buckingham Avenue, the safety rules about staying on the sidewalk really matter.
Proceeds go to three local causes: Milford Public Schools, Purple Pantry Boxes, and Avery's Little Army, which supports pediatric cancer patients and awareness.
Pick up your bib early
With this many people, the organizers ask participants to collect their shirts, bibs and packets before Thanksgiving morning, because they can't handle that much traffic at the start. These are the tentative early-pickup times. The organizers will confirm them by email closer to the event:
- Saturday, November 21, 10 a.m. to 1 p.m., Dick's Sporting Goods
- Sunday, November 22, 11 a.m. to 2 p.m., Dick's Sporting Goods
- Monday, November 23, 6 to 8 p.m., Shoreline Family Chiropractic
- Wednesday, November 25, 4:30 to 7 p.m., Turkey Trot HQ, 31 Wilbar Ave.
The shirt guarantee covered people who registered before November 3. For anyone registering after that, the organizers say they'll do their best to provide one, but they can't promise it. The organizers also have volunteer slots open for anyone who would rather help than walk.
Where the canned goods go
The Trot asks everyone to bring shelf-stable food for Purple Pantry Boxes. Any shelf-stable food helps, but these are the items it needs most: tuna, peanut butter, nuts, sardines, canned ham, soup, pasta and cereal. The race page says Milford residents have voted the group best local cause, an award from the Milford City Chamber of Commerce, several years running.
Purple Pantry Boxes was started by Sue Brown in March 2020 with three plastic bins. The bins later became wooden pantry boxes. Anyone can take what they need, with no application and no ID. The boxes are another piece of public, open-air setup. They sit in parking lots and outside community buildings across town, and you can spot them by their bright colors. Milford sites on the group's locations page include:
- Senior Center, 9 Jepson Dr.
- Catherine McKeon Village, 73 Jepson Dr.
- The parking lot at Ormand St. and Bridgeport Ave.
- YMCA, 631 Orange Ave.
- DeMaio Gardens, 75 DeMaio Dr.
- MAC Gallery, 81 Naugatuck Ave.
- United Way, 20 Evergreen Ave.
- Woodmont United Church of Christ, 1000 New Haven Ave.
- Elks Lodge, 124 New Haven Ave.
- Foran Towers, 264 High St.
- United Presbyterian Church, 109 Seaside Ave.
- Island View Terrace, 100 Viscount Dr.
- Mary Taylor Memorial United Methodist Church, 176 Broad St.
The Elks Lodge and Woodmont United Church of Christ boxes are both on New Haven Avenue, the same road the full Trot loop uses on its way back. The Senior Center on Jepson Drive comes up again on Saturday as a free parking lot for the downtown market.
Saturday: the Green without the library
Two days after the Trot, the Downtown Milford Business Association holds Small Business Saturday on Saturday, November 28, from 10 a.m. to 3 p.m. on the Milford Green, 84 S Broad St. It's free.
The format has changed. Last year's event, on November 29, 2025, used the Milford Green, Taylor Memorial Library and participating downtown businesses, and the association billed it as 60+ indoor and outdoor vendors. For 2026, the association says the event will be held outdoors only. The library is no longer a vendor space, so the Green and the storefronts around it carry the whole day. Plan to stay outside, and dress for it.
What the association has announced for this year:
- 60+ vendors, including food trucks and food vendors, selling arts and crafts, clothing, jewelry and home décor
- 10+ storefronts taking part, including restaurants, spas and bookstores
- A punch card: the first 250 shoppers to complete the Small Biz Saturday card get a Shop Local Milford tote bag with deals from association members
Patch reported the same plan on October 30, with the pop-up running on the Green and at participating downtown businesses.
Free parking for Saturday
The association lists these free lots, many of them a short walk from the Green:
| Lot | Address |
|---|---|
| Harborside Middle School | 175 High St. |
| New public parking | under 44 River St. |
| Armory Square / Harborwalk | 22 Broad St. |
| Lisman Landing | 37 Helwig St. |
| Senior Center | 9 Jepson Dr. |
| Near Milford Green | Broad St. |
| Wasson Field | 108 W. Main St. |
| Parsons Government Center | 70 W. River St. |
The same Saturday, the Milford Regional Chamber calendar lists Miss Dallas' Shop Holiday Shopping Extravaganza at 16 Higgins Drive from 9 a.m. to 5 p.m., with work from 29 local artisans. It runs longer than the downtown event on both ends, so you can fit in both.
After the weekend, the Green stays busy
Small Business Saturday is the first of three free holiday events the Downtown Milford Business Association has planned, according to Patch.
- The 24th annual Lamplight Stroll is Friday, December 4, from 5 to 9 p.m. on the Milford Green and at participating businesses. It brings Santa and his elves, horse-drawn carriage rides, carolers, holiday vendors and hot cocoa. A Stroll Passport Adventure asks you to collect more than 20 stamps for a chance at prizes.
- Sip & Shop is Thursday, December 17, from 5 to 8 p.m. at participating downtown stores, including Bond & Co, Whispers, Inside Living Style, Makeup Makeup and Mind Body Wellness.
Put together, Milford's holiday season runs from Gulf Street sidewalks on Thanksgiving morning to the Green on November 28 and back to the Green on December 4.
Thanksgiving is our favorite stretch of the year at Grasso Team, and giving back locally is a big part of it for us too. Take a look at our 2026 Thanksgiving Pie Event and our Thanksgiving Blessing Basket to see how we're marking the season. If you're walking the Trot loop or shopping on the Green and want to talk about what's next for your home, we'd be glad to hear from you. Contact Us anytime.
