Wellesley Hills Halloween Stroll 2026: A Guide to Fall Reopenings

"You just don't see architectural details like this in your normal daily life anymore," interior designer Richard Eustice told The Swellesley Report on the day the Wellesley Hills Branch Library reopened. "Libraries are one of the few places this kind of detail still exists."

He meant a building from 1928. Three days later, farther up Washington Street at No. 300, Maugus Cafe held its grand reopening. The cafe has anchored the village since the 1930s. At No. 207, Wellesley Hills Congregational Church set out its pumpkin patch for the 23rd year. This fall the Hills got its biggest changes by renovating the places it already had, mostly with neighborhood money and volunteer hours. On Saturday, Oct. 31, the Town's Halloween Stroll starts at Clock Tower Park, No. 291, which puts it in the middle of that refreshed stretch.

The library got its 1928 room back

The Hills branch at 210 Washington Street reopened on Oct. 6. It had been closed for four months for an interior refresh. The building is a Georgian Revival listed on the National Register of Historic Places, and it has served as a library since March 20, 1928. Its 100th anniversary is a little more than a year away.

Most of the work brings back what was already there. The original plaster friezes had been painted pink at some point, and they are now crisp white again. The main room keeps its original reading tables. The new carpet uses an Arts and Crafts tile pattern, and the library's original 16-by-16 cork floor tiles from 1928 still lie underneath it. The overhead fixtures were hand-cast in bronze and alabaster by a Milwaukee firm that makes period lighting. The Children's Room has new hardwood floors and a storybook mural by Jason Sawtelle of BlackBeak Studios, the same artist who painted the 2018 murals at the Fells Branch Library.

The Hills has kept this building open before. In 2005, budget limits shut the branch. Private donations reopened it in 2008. Even in 1928 it was a shared project: Isaac Sprague, the namesake of Sprague Clocktower Park, donated the land, and the Wellesley Hills Women's Club furnished the Children's Room. This time Nancy Lee provided the seed money and much of the funding, along with a grandfather clock now in the building. Keith Higgins, the Wellesley Free Library Foundation and many private donors also gave significant support.

Maugus kept the stools

Maugus Cafe at 300 Washington Street changed hands in 2025. The Papakonstantinou family had owned and run it for nearly 45 years, and the new owner is Kostas Saranteas. A soft opening over the summer led up to the Oct. 9 grand reopening, which the cafe held off on until school was back in session.

The renovation followed the same idea as the library: change the room and keep the things people know. The Swellesley Report's July feature found the counter stools, booths and group tables still in place. The red carpet is gone. There is a new counter facing Washington Street, plus outdoor tables. Breakfast and lunch staples stayed on the menu, and the new additions lean Mediterranean and Greek: Atomic coffee, six omelette styles, a souvlaki bowl and a Greek Village Salad.

Hours could change next. In early October, the Select Board approved amendments to the cafe's common victualler and all-alcohol licenses. Before that, Maugus had been open until 5 p.m. every day, with Saturday and Sunday starting at 7:30 a.m. The amendments allow 7 a.m. to 10 p.m., seven days a week. As of the Oct. 7 report, dinner on select days was planned for the coming months, so call ahead before you plan a Halloween supper there.

Volunteers run the pumpkins, and a garden is about to open behind them

The pumpkin patch at Wellesley Hills Congregational Church, 207 Washington Street, is open 10 a.m. to 6 p.m. daily, and Saturday is its last day. Proceeds go to an outside charity and to the church's Youth Fellowship for its annual service trip. Parishioner Janeen Hansen, who volunteers at the patch every year, told The Swellesley Report in mid-October that "a second truckload of pumpkins is on its way!" Wagons are available if one pumpkin turns into four.

Behind the east side of the church, Mainstay Landscape has been finishing a new contemplative garden in a small pocket of land. On Oct. 16, the same outlet reported it would open to the public "in a couple of weeks," which puts the opening right around Halloween weekend. If it is open, pair it with the labyrinth in Clock Tower Park, which the Town maintains together with the Wellesley Hills Garden Club.

Saturday on Washington Street, address by address

The Halloween Stroll runs 11 a.m. to 1 p.m. on Saturday, Oct. 31. The Wellesley Recreation Department and the Wellesley Hills Merchants host it, and it is aimed at children up to age 8. It starts at the Clock Tower at 291 Washington Street, across from Green's Hardware. Kids walk at their own pace, trick-or-treat at shops along the way, and come back to the park for games and music. Bring your own bag, because the Town asks you to.

The Town has not posted a 2026 list of participating businesses. Its 2025 roster shows the kind of stops involved: Green's Hardware, Caffe Nero, Quebrada Baking Co., Jejes Coffee House, Pho Station, Coconut Thai Cafe, Marathon Sports, Peaceful Pooch, Ideal Barber Shop, Holly Cleaners and the Wellesley Hills Library were all stops last year.

Here is how the fall's changes line up along Washington Street on either side of the Stroll's starting point:

Most of what is new on that list either reopened at an old address or is moving a few blocks down the same street. The only arrivals are a spa that opened in June and a fitness studio that is still coming.

In Wellesley Square, change is on a longer clock

Wellesley Square is changing too, but on a planning schedule. The Wellesley Square Improvement Project held the first of four public meetings on Oct. 14. Construction funding is expected to be requested in 2028. The next meeting, scheduled for Nov. 18, will cover refined design alternatives.

On Central Street, the Taylor Block storefronts where Comina and Panoply used to be were still papered over and marked for lease as of mid-October. The Swellesley Report reported that owner Jumbo Capital was unlikely to act on that block for five years while it focuses on 888 Worcester Street. Our summer look at Wellesley Square followed the owner-operators filling the Square's other storefronts. In the Hills, the work was done by a single cafe owner, a list of library donors and a church that runs a pumpkin patch. Those projects are already open, and the Square's plan has construction funding expected to be requested in 2028.

After the Stroll, and after Saturday

The afternoon is open for pumpkins until 6 p.m. Then the evening follows a routine The Swellesley Report describes this way: the youngest trick-or-treaters go out in their own neighborhoods around 6 p.m., older kids head out around 6:30, and most houses turn off their porch lights around 8. Halloween falls on a Saturday this year, so nobody has school the next morning.

After that, the Hills calendar turns to things that are still pending. Pvolve is targeting winter at 251 Washington Street. Middlesex Savings Bank has not set a date for its move from 278 to 390 Washington Street, at Forest Street. Dinner at Maugus is planned but not yet announced. Elsewhere in town, Wellesley Marketplace brings more than 200 artisans and local businesses to Wellesley High School, 50 Rice St., on Saturday, Nov. 21, from 10 a.m. to 4 p.m., with VIP entry at 9. For more on how the Hills compares with Wellesley's other villages, see our Wellesley neighborhood guide.

If you own a home near Washington Street and wonder how a fall of reopenings on your block shows up in what your house is worth, Diane Basemera can walk you through it, one Hills address at a time. Start with your instant home valuation.