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Monroe CT October Events 2026: Think Pink and Halloween

"We really have been happy about it, because we can support people in Monroe," Bonnie Maur told The Monroe Sun last week, speaking about the nonprofit she founded in 2019. Maur is a retired Monroe teacher. Her group, Think Pink Monroe, opened the month with Pink Palooza on the town green on Sunday, Oct. 4. The afternoon had a cornhole tournament, music from Masuk High School's chorus, orchestra and band, and a talk by Monroe resident Alexandra Belluzzi.

That same Sunday evening, the Monroe Historical Society held two sessions of "An Evening With Hannah Cranna" at East Village Meeting House on Barn Hill Road. Those two events set up the rest of October. One thread is a breast cancer awareness campaign spread across Monroe's sports teams, fitness studios and gathering spots. The other is a Halloween season that starts with local folklore. In the back half of the month, the Edith Wheeler Memorial Library carries most of it.

A Campaign Built to Keep Its Dollars in Monroe

The shape of Think Pink's calendar follows from how the group spends its money. It worked closely with St. Vincent's Swim Across the Sound before it became an independent nonprofit four years ago. Since then its financial help has gone only to Monroe residents, although its support groups welcome people from other towns.

Two changes this year show the group adjusting to what local patients actually use:

  • Larger grants. The most a patient can receive in assistance has gone from $500 to $1,000. The money can go to whatever eases daily life, from medical bills to gas and food.
  • Copays in place of a screening truck. In past years the group brought a mammogram truck to town, but people did not sign up for the time slots. This year Think Pink will pay up to $300 per person toward uninsured costs or copays for diagnostic breast cancer tests.

The group also arranges rides to treatment when it can. Maur said that growing further depends on recruiting volunteers. "I would love to see us grow with more businesses in town," she added. October's schedule reflects that goal. Instead of one large fundraiser, the events are spread among Masuk teams, two fitness studios and a Main Street gathering place.

The Think Pink Dates Still Ahead

Masuk teams are holding Pink Day games to raise money through the third week of October. Girls swimming already held its game on Oct. 2.

  • Cross Country, Oct. 6
  • Girls Soccer, Oct. 8
  • Football, Cheer and Dance, Oct. 16
  • Field Hockey, Oct. 19
  • Boys Soccer, Oct. 20
  • Girls Volleyball, Oct. 22

The group's own events run alongside the games:

  1. Pink Farmers Market, Friday, Oct. 9
  2. Think Pink Walk at Great Hollow Lake, Saturday, Oct. 10, 11 a.m.
  3. Heart of a Lion Day, Friday, Oct. 16
  4. CycleBar Ride, Saturday, Oct. 17, 8 a.m.
  5. Row House Ride, Saturday, Oct. 24, 9:15 a.m.
  6. Pink-Out Party at Monroe Social, Tuesday, Oct. 27

Maur said the two studio rides are new this year. Both studios are in Century Plaza at 535 Monroe Turnpike. Row House is in Unit C2, near Cross Hill Road. Monroe Social, where the month ends, is at 494 Main Street.

You can also help without signing up for an event. Pass the Pink starts with an empty pink basket. One person adds a comfort item for someone in treatment and passes the basket to a friend or neighbor, who adds another. Finished baskets go to the nonprofit, which gives them to people who have just been diagnosed. Raffles run all month, and a silent auction features a handmade quilt made by a survivor. To volunteer, email [email protected] or call Maur at 203-339-1753. Assistance applications and donations are on ThinkPinkMonroe.com.

Hannah Cranna Started the Halloween Side

Monroe's Halloween season began on the same weekend as Pink Palooza. The town calendar listed an East Village Cemetery Lantern History Walk from 5 to 8 p.m. on Oct. 3 and Oct. 4. On Sunday, the Historical Society held its Hannah Cranna program at 6 p.m. and again at 8 p.m. Admission was $10, with light refreshments.

Two different stories surround her. In the folk version, which The Monroe Sun traced to a book by Edward Nichols Coffey, "Cranna" was a teasing nickname for a woman who may have been Hannah Hovey. She lived around Cragley Hill in the Bug Hill and Cutler's Farm area. According to the legend, villagers tried and failed to move her coffin, finally buried her just over the line in Trumbull, and her house burned.

The Historical Society's own historian, Kevin Daly, tells a calmer story. He identifies her as Hannah Tomlinson-Hovey, who lived from 1763 to 1831 and settled with her husband, James, on a Monroe farm near Old Newtown Road. Daly writes that she, her husband and their five children are buried at Long Hill Burial Ground in Shelton. So the legend places her grave in Trumbull, and the historical record places it in Shelton.

Two Saturdays Carry the Middle of the Month

Most of Monroe's mid-October events fall on two Saturdays.

Saturday, Oct. 10

  • The Edith Wheeler Memorial Library holds its all-ages Halloween Vendor Fair from 9:30 a.m. to 1:30 p.m. on the town green and library lawn. It is drop-in, with no registration.
  • The Monroe Women's Club Halloween Costume Collection is on the town calendar from 10 a.m. to 5 p.m. No location is listed.
  • The Think Pink Walk starts at Great Hollow Lake at 11 a.m.

The next morning, Sunday, Oct. 11, Board & Brush Monroe at 292 Elm St. celebrates its 10th anniversary. The open house runs from 10 a.m. to 2 p.m., with $20 mini-projects and giveaways.

Saturday, Oct. 17

  • The Think Pink ride at CycleBar starts at 8 a.m.
  • A Trunk or Treat Car Show is on the town calendar from 9 a.m. to 2 p.m. Check the venue before you go, because the listing does not include one.
  • Stepney Volunteer Fire holds Bingo Night at Station One, 88 Main St. Doors open at 5:30 p.m., and games start at 6:30 p.m.

Great Hollow Lake also hosted the 9th annual Chasing Ciara's Light 5K and 12K trail race on Oct. 3, so the Think Pink walk is the park's second organized event of the month.

After Oct. 18, the Library Carries the Calendar

When we checked, the town's online community calendar showed no events after Oct. 18. Besides Think Pink's Row House ride and Pink-Out Party, nearly everything on the late-October schedule comes from the Edith Wheeler Memorial Library:

  • Monday, Oct. 19: "Take & Make: Ghost Window Clings," 9 a.m. to 2 p.m.
  • Monday, Oct. 26: Teen Halloween Party and Movie Night, 6 to 8:30 p.m., with costumes, snacks, activities and a screening of "Ghostbusters."
  • Tuesday, Oct. 27: Paranormal researcher Joe Franke presents "Based on a True Story": Separating Fact from Fiction in Hollywood's Horror Films, 6 to 7:30 p.m., for teens and adults.
  • Wednesday, Oct. 28: Teen Halloween Escape Room, 3 to 5:30 p.m.
  • Friday, Oct. 30: Preschool Halloween Parade, 10:30 to 11 a.m. The group walks past the library, Town Hall and the Police Department, and no registration is required.

Two other events fill the gaps. On Sunday, Oct. 25, Harmony Grange No. 92 at 103 Hurd Ave. hosts a beginner mandala painting workshop from 3 to 5 p.m. And Oct. 27 is the month's busiest evening, with Franke's horror-film talk at the library on the same night as Think Pink's Pink-Out Party at Monroe Social.

We found no confirmed Monroe event for Halloween night itself in the sources we checked. As of this writing, the library's Oct. 30 parade is the last listed event of the month.

Elizabeth Casey has worked in and around Monroe for more than 30 years, long enough to know that a town's character shows up in calendars like this one. If you are thinking about how your own home fits into Monroe's market this fall, Elizabeth Casey can give you a clear local read. Get Your Instant Home Valuation, and then let's talk it through.

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