On Saturday, October 31, the pumpkins in front of Wellesley Hills Congregational Church will be on sale for the last time this year. Across Washington Street, families with toddlers in costume will start gathering at Clock Tower Park well before the 11 a.m. start of the Halloween Stroll. By evening the village will be quiet again, and Halloween moves out to the neighborhoods, where porch lights go on around 6 p.m. and go dark around 8.
When Halloween falls on a weekday, those pieces land on different days or get squeezed around school and work. This year they all land on one Saturday. For most of the day, the busiest Halloween spot in Wellesley is a short stretch of Washington Street in the Hills. That stretch also has more going on than it did last October, because a longtime restaurant and the branch library have reopened there since the summer, and a new garden is due to open around the end of the month.
| Time on Oct. 31 | Where | What happens |
|---|---|---|
| 10 a.m. to 6 p.m. | Wellesley Hills Congregational Church, 207 Washington St. | Last day of the Pumpkin Patch |
| 11 a.m. to 1 p.m. | Clock Tower Park, 291 Washington St. | Halloween Stroll: trick-or-treating at Hills businesses, plus games and music in the park |
| Midday into evening | Maugus Cafe, 300 Washington St. | Recently reopened, with new hours approved |
| Around 6 p.m. | Neighborhoods across town | Younger trick-or-treaters head out |
| Around 6:30 p.m. | Neighborhoods across town | Older kids follow |
| Around 8 p.m. | Neighborhoods across town | Porch lights go off |
The patch has its final day
The Wellesley Hills Congregational Church Pumpkin Patch has been open at 207 Washington St. every day since October 9, from 10 a.m. to 6 p.m., and it closes on Halloween. This is its 23rd year, and The Swellesley Report's Halloween roundup calls it "one of Wellesley's beloved annual traditions."
Everything on the lawn is for sale, at a range of prices, and the church provides wagons for shoppers who leave with more than one. Parishioner Janeen Hansen, who volunteers at the patch every year, told The Swellesley Report in mid-October, "The patch is a great fundraiser, and a second truckload of pumpkins is on its way!" The church splits the proceeds between an outside charitable organization and its Youth Fellowship, which uses the money for its annual service trip.
If you stop at the patch on Saturday morning, you will already be on the block where the Stroll starts an hour later.
Eleven to one: the Stroll
The Wellesley Recreation Department's Halloween Stroll runs from 11 a.m. to 1 p.m. and starts at Clock Tower Park, 291 Washington St. It is free and aimed at children up to age 8, who come in costume, walk to trick-or-treat stops and play games. Bring your own bag. The Swellesley Report's Halloween roundup places the start across from Green's Hardware and says the park will have games, music and other treats for the full two hours.
The town's 2026 participant roster lists 31 stops. Taken together, they give a good picture of everyday life in the Hills village:
- Food and coffee: Quebrada Baking Co., Jejes Coffee House, Caffe Nero, Pho Station, Coconut Thai Cafe, Comellas, Liliko Market
- Everyday errands: Green's Hardware, Holly Cleaners, Ideal Barber Shop, The Windsor Press, Marathon Sports, Capezio, A Custom Clothiers
- Pets: Peaceful Pooch, Boston Veterinary Clinic
- Community institutions: Wellesley Hills Historical Society, Wellesley Hills Library, UU Wellesley Hills, Wellesley Hills Center for Early Education
Banks, a dental office, a tile showroom and a wellness practice fill out the rest of the list. Compared with the 2025 roster, the one new name this year is Liliko Market.
The roster also invites the grown-ups to take part. A Wellesley Recreation table in Clock Tower Park will take votes for Best Dressed Business Staff and Best Decorated Business, and the winning businesses receive a prize. In other words, the shops are competing too, so it pays to look at the windows as well as the costumes.
The town has not published a rain plan for the Stroll, so check the Recreation calendar listing on Saturday morning if the weather looks uncertain.
After one o'clock: two reopenings and a garden on the way
For families who want to stay in the village after the Stroll, two familiar places nearby have reopened since the summer, and a third is a brand-new space expected to open around Halloween.
Maugus Cafe, 300 Washington St. Maugus has been in its storefront across from Clock Tower Park since the 1930s, and the Papakonstantinou family ran it for nearly 45 years. According to The Swellesley Report's July profile, new owner Kostas Saranteas removed the red carpet but kept the counter stools and booths. He also added counter seating facing Washington Street and outdoor tables. The menu still centers on diner-style breakfast and lunch, now with Mediterranean dishes such as a spanakopita-style omelette, a souvlaki bowl and a Greek village salad. The coffee comes from Atomic Coffee Roasters.
After a soft opening over the summer, the cafe held its grand reopening on October 9. That same week, the Select Board approved license changes that let it stay open from 7 a.m. to 10 p.m. seven days a week. Its previous hours ended at 5 p.m. As of early October, dinner service on select days was still planned for the coming months. Call ahead before counting on an evening meal there on Halloween.
Wellesley Hills Branch Library, 210 Washington St. The Hills branch reopened on October 6 after a four-month closure for an interior refresh. The Georgian Revival building has been a library since March 20, 1928, so its 100th anniversary is less than two years away. It sits on land donated by Isaac Sprague, the namesake of Sprague Clock Tower Park. Budget constraints closed the branch in 2005, and private donations reopened it in 2008. The library is also a Stroll stop this year, so families will see the refreshed interior on their way through.
A new contemplative garden behind Hills Church. Mainstay Landscape was finishing a garden in a small space behind the east side of the church in mid-October. The church expected to open it to the public a couple of weeks later, which would put the opening near Halloween. That date was an estimate, so the garden may or may not be open on the 31st. If it is, The Swellesley Report suggested pairing it with a stop at Clock Tower Park, which the Town maintains with the Wellesley Hills Garden Club and which has a labyrinth.
So for one long Saturday morning and afternoon, the stretch around Clock Tower Park offers pumpkins, trick-or-treating, a newly reopened diner and a newly reopened library within a short walk of one another.
Six to eight: back to the neighborhoods
At dusk, Halloween moves from the village to residential streets across town. The Swellesley Report describes Wellesley as "definitely an October 31st trick-or-treating kind of town." Younger children usually go out in their own neighborhoods around 6 p.m., older kids around 6:30, and most houses switch off their porch lights and blow out their jack-o'-lanterns around 8 p.m. to show they are done for the night. The same report says the timing "can vary from neighborhood to neighborhood, but not by much."
A Saturday Halloween means no school the next morning, a point the Swellesley roundup made too. In practice, families who start with pumpkins at 10 a.m. and the Stroll at 11 still have the whole afternoon to rest before the neighborhood rounds at 6. If you are giving out candy, plan to have the porch light on and the bowl full by about 6 p.m., since that is when the youngest trick-or-treaters start. If you live in or near the Hills, the evening will be much calmer than the late morning on Washington Street.
Several Wellesley Hills fixtures, from Maugus Cafe's counter to the library's Georgian Revival reading room, have recently reopened or changed hands, and that is part of what Laura pays attention to in the village. If a move within town or a first home in the Hills is on your mind for next year, Laura Wurster is happy to talk it through over coffee, and Maugus is right across from the park.
