Last year, Wellesley Hills held its Halloween Stroll on Saturday, October 25. Costumes came out, merchants handed out candy, and then most families waited six days for the real thing.
This year Halloween is a Saturday, and the Town of Wellesley's 2026 calendar lists the Stroll for October 31 itself, from 11 a.m. to 1 p.m., starting at Clock Tower Park, 291 Washington Street. Moving it onto the holiday changes how the day works. The morning on Washington Street and the evening on your own street are now two halves of the same Halloween.
Here is the day in order, then the details that matter.
Friday to Saturday night, in order
- Friday, October 30, 10:30 to 11:15 a.m. Wellesley Free Library runs a drop-in Halloween Storytime in the Wakelin Room at the Main Library, with stories, songs, a craft, a costume parade and trick-or-treating around the building.
- Saturday, 10 a.m. The Wellesley Hills Congregational Church Pumpkin Patch opens for its final day at 207 Washington Street.
- Saturday, 11 a.m. to 1 p.m. The Halloween Stroll runs from Clock Tower Park along Washington Street.
- Saturday, 6 p.m. According to The Swellesley Report's 2026 Halloween roundup, the youngest trick-or-treaters usually head out around 6 in their own neighborhoods, with older kids following around 6:30.
- Saturday, around 8 p.m. Most porch lights go off and the jack-o'-lanterns get blown out, the same roundup notes. It adds that timing varies a little from neighborhood to neighborhood.
The pumpkin patch closes at 6 p.m., right as the neighborhood rounds begin. If you still need a pumpkin for the front steps, you have until then.
The Stroll, block by block
The town describes the Stroll as a joint event of the Wellesley Recreation Department and the Wellesley Hills Merchants. It's built for children ages 0 to 8, who walk at their own pace and trick-or-treat at stops along the way. There are games at the Clock Tower, and the town's one firm instruction is to bring your own trick-or-treat bag.
The 2026 participant roster lists each stop by street number, which turns it into a map. Stops run from 239 to 356 Washington Street, with Clock Tower Park at 291 near the middle. You can start at the park and head either way without doubling back much. One stop sits apart from the rest: Wellesley Gas at 431.
| Washington St. numbers | Stops on the 2026 roster |
|---|---|
| 339 to 356 | The Windsor Press, Pho Station, Bank of America, Caffè Nero |
| 324 to 336 | Capezio, A Custom Clothiers, Art of Tile & Stone, Wellesley Hills Historical Society, Wellesley Hills Library, Wellesley Hills Center for Early Education, First Citizens Bank |
| 298 to 316 | Stepping Stone Acupuncture & Wellness, UU Wellesley Hills, Green's Hardware, Wellesley Family Dental |
| 272 to 290 | Holly Cleaners, Comella's, J.P. Morgan, Middlesex Bank, Quebrada Baking Co. |
| 255 to 268 | Liliko Market, Home Décor Group, Ideal Barber Shop, Jejes Coffee House, Coconut Thai Cafe, Marathon Sports |
| 239 to 245 | Peaceful Pooch, Boston Veterinary Clinic |
| 431 | Wellesley Gas |
A few more stops on the roster are left out of the table, so expect a handful of extra doors along the way. For a two-hour event aimed at children eight and under, the stretch from 245 to 356 is plenty. With a toddler, one side of the park can be a full morning.
The roster also lists the stops that make good pauses: a coffee at Caffè Nero or Jejes Coffee House, a pastry from Quebrada Baking Co. at 272, and Green's Hardware at 308, which sits across from the park and anchors the start.
The merchants are competing, too
The bottom of the roster shows that the Stroll includes a contest for the businesses. Families vote for Best Dressed Business Staff and Best Decorated Business at the Wellesley Recreation table in Clock Tower Park, and the winners receive a prize.
That makes the walk down Washington Street a judging circuit too. If you're the family that notices the barber in a cape or the staff dressed as a theme, the ballot is where that counts. The voting table is at the park, so the vote fits naturally at the end of the loop, before the games.
The newest door on the route
Liliko Market at 268 Washington Street is the stop most families won't have known a year ago. The Swellesley Report describes it as an Asian convenience store that opened over the summer. This week it won Select Board approval for a take-out common victualler license.
The same report says the shop is installing a hot-water station and a microwave, so customers can prepare packaged food on site and take it to go, with the Health Department coordinating. The work was still underway in the October 21 report, so whether it's running by Saturday is up to the shop. Liliko's first Halloween on Washington Street arrives just as it's adding that service.
The pumpkin patch's last day falls on the same morning
The Pumpkin Patch at Wellesley Hills Congregational Church is in its 23rd year, open 10 a.m. to 6 p.m. daily through October 31. The church at 207 Washington Street is a short walk below the lowest Stroll stops, so the patch can open or close the morning.
The town's calendar lists the patch as a fundraiser for the Youth Service Trip and the Wellesley Food Pantry. In The Swellesley Report's visit to the patch, parishioner and longtime volunteer Janeen Hansen called it "a great fundraiser" and said a second truckload of pumpkins was on its way. The same piece notes that wagons are available for shoppers.
The church has another reason to linger. The same report previewed a new contemplative garden by Mainstay Landscape, tucked behind the east side of the church and getting its finishing touches in mid-October. At the time it was expected to open to the public "in a couple of weeks," which could put the opening close to Halloween weekend. The writer suggested pairing it with Clock Tower Park, maintained with the Wellesley Hills Garden Club, and its labyrinth for a two-garden tour of Wellesley Hills. If the new garden has opened by Saturday, that tour runs between the patch and the starting line of the Stroll.
After dark, the route moves to your street
When the Stroll ends at 1 p.m., the action moves back to the neighborhoods. Wellesley has its own Halloween contest for houses. The Recreation Department posted the Howlin' Haunted Halloween House Decorating Contest 2026 on October 7. According to The Swellesley Report's roundup, it has two categories, "Scariest" and "Judges' Choice." Nominations went to Recreation by email with a photo and address, and closed Wednesday, October 28. Awards are delivered by Rec's Boo Crew. If a house on your block went all out, Saturday night is its biggest audience.
The evening itself runs on custom. The Swellesley Report calls Wellesley "an October 31st trick-or-treating kind of town." It says some houses are known for handing out full-size bars, and it declines to say which ones. It also points out that a Saturday Halloween means no school the next morning. Put that together with a Stroll on the same day, and a child in Wellesley Hills can trick-or-treat at 11 a.m. on Washington Street and again at 6 p.m. at home.
Molly Campbell Palmer is based in Wellesley and works the same Wellesley Hills blocks that fill with costumes on Saturday. If you want to know what a house on your trick-or-treat route is worth, Molly Campbell Palmer can start with a quick number. Get your instant home valuation.
