
Hello, Dedham.
If you’re waiting until Halloween to turn your heat on, good news—it’s creeping up. Also, early voting is open, Saturday is stacked with fun, and the skies are putting on a show. Grab your favorite blanket and lets dive in.
In this week's Drop:
Trunk or Treat and trick-or-treating in the Square on Saturday
Voter registration and mail-in ballot deadlines this week
A new logo for the Town Green, and you could design it
Glad you're here!
KB
📰 Digest
🎨 Design the Town Green's new logo: The Friends of the Dedham Town Green are looking for a fresh logo. The winner gets $250 in gift cards to the Dedham Square business of their choice, recognition in the Dedham Times and on the Friends' website and social media, and a framed copy of the logo. It's open to everyone, up to 3 designs, and no AI. Hand-drawn is welcome. The logo must include "Friends of Dedham Town Green." Under-18 entrants need a parent or guardian's permission. Entries are due Friday, 11/6 by 11:59PM. Email [email protected] with the subject "Logo Submission," or mail a printed design to Friends of Dedham Town Green Logo Contest, 601 High Street, Suite 204.
🏛️ Last call on the town's buildings: The Facilities Master Plan Steering Committee's quick Menti survey closes Friday, 10/23. The committee and consultant Arrowstreet will review the feedback so far at a public meeting on Monday, 10/26. Want the building-by-building needs first? Start here.
🐮 Dedham Day is Saturday, 11/7 (rain date 11/8) at Barnes Memorial Park. Grab your Cow Plop deeds here.
✳️ Got a local announcement? Hit reply and let me know.
📆 What’s Happening
Thursday, 10/22
🖌️ Watercolor class registration opens at 9AM for the library's November classes (11/5 and 11/19).
🌳 Town Green Donor Plaque Unveiling: 5:30PM at the Town Green, 600 High St. Remarks from Town and Friends of the Dedham Town Green leadership, then the unveiling of plaques honoring the donors who helped make the Green possible. Parking is in the Keystone Lot, Town Hall lots, and nearby streets.
Friday, 10/23
🎃 Halloween Concert with Vanessa Trien & The Jumping Monkeys: 6–7PM on The Green at Legacy Place, near J.Crew. A family-friendly Halloween show from the Parents' Choice Award-winning Boston kids' band. Free, but tickets are required for everyone through the Legacy Place Insider app.
Saturday, 10/24
🍬 Trunk or Treat & Dedham Square Trick-or-Treating: Free, and all towns are welcome. Trick-or-treat in the Square from 2–5PM. Trunk or Treat is in the Registry of Deeds lot from 3–5PM, with a sensory-friendly hour at 2:30–3PM. Live music on the Town Green runs 4–6PM. Rain date is 10/25. Volunteers needed; sign up on the DSC site.
Monday, 10/26
🎵 Monday Morning Music: 9:30AM and 10:30AM at the Endicott Branch lawn. For babies, toddlers, and preschoolers.
🎹 Music with Michael: 6:30PM at the Main Library. A musical evening with pianist Michael Leidig.
Tuesday, 10/27
👥 Dedham Junior Women's Club General Meeting: 7PM at the Endicott Estate. All are welcome, and light refreshments are served.
Wednesday, 10/28
🎶 Halloween Music & Movement with Rockabye Beats: 10:30AM at the Main Library. Singing, dancing, rhythm instruments, and Halloween songs.
⚡ Pokémon Club: 3:30PM at the Endicott Branch.
👁️ Glowing Eyeball Jar for Teens: 5:30PM at the Main Library. Creepy Halloween decor.
Thursday, 10/29
🐕 Read to Barkley the Therapy Dog: 5:30–6:30PM at the Main Library, in 15-minute slots. 5:30 and 6:15 are open as of 10/21.
Saturday, 10/31 🎃
🍿 Movie Matinee: Minions & Monsters: 10AM–12PM at the Main Library, in the Children's Room. A good plan before trick-or-treating.
🎶 Live Music
FRI 10/23
🎃 Vanessa Trien & The Jumping Monkeys: 6–7PM at Legacy Place (details above).
SAT 10/24
🎶 Concerts on the Green: Free fall concert on the Town Green in Dedham Square, with dinner or a treat from one of the Square's eateries. Featuring: The Ukuladies (50s-to-today hits), 4–6PM. Free parking in the Keystone lot at 10 Eastern Ave.
🎸 The Love Dogs: 7PM at The Fallout Shelter in Norwood.
🏃 Activities & Sports
🥎 Dedham Girls Softball, Sunday, 10/25:
1:00PM: 10U summer tryouts at Churchill Field. Bring your glove, face mask, and water. Cleats preferred but not necessary.
3:00PM: Pitching clinic evaluation at Sugrue Field. A trial for any player interested in pitching, run by pitching coach Aimee Sullivan.
⚾ For everything youth sports, check each program's own site: Baseball | Soccer | Youth Hockey | Lacrosse | Field Hockey | Youth Football | Basketball | Girls Softball
Sport leagues — have an upcoming tryout? looking to fill board seats? hosting a clinic? Hit reply & let us know so we can share your updates here!
📌 HIGH SCHOOL SPORTS: Dedham | Nobles | Ursuline & streaming on NFHS Network for Dedham High home games.
🏛️ Civics class
🗳️ Early voting is open for the November 3 State Election (polls open at 7AM on Election Day). In-person early voting runs through 10/30 at Town Hall, Meeting Room 304. Hours:
Thursday, 10/22: 8:30AM–4:30PM
Friday, 10/23: 8:30AM–1PM
Saturday, 10/24: 9AM–3PM
Week two has the same pattern, 10/26 through 10/30
You can view the sample ballot here.
📅 Two deadlines worth a calendar reminder: Saturday, 10/24 is the last day to register to vote, with the Town Clerk's Office open 9AM–3PM. Tuesday, 10/27 at 5PM is the last day to request a mail-in ballot. Questions: 781-751-9200.
📋 On the town calendar this week:
📋 Thursday, 10/22: Select Board, 6:30PM · Public hearing on the proposed layout plan to reestablish Whiting Ave. and Walnut St. as public roadways, 6:30PM (O'Brien Meeting Room, 3rd floor, Town Hall)
♻️ Monday, 10/26: Conservation Commission site visit at 37 Icehouse Lane, 2PM · Facilities Master Plan Steering Committee public meeting
📖 Tuesday, 10/27: Historic Districts Commission/Historical Commission, 7PM
📆 Wednesday, 10/28: Planning Board, 6PM
🏘️ Town Hall to Your Neighborhood: Hear from department heads, learn what's happening in your neighborhood, and ask staff questions directly. All sessions start at 6:30PM.
Monday, 11/30: Avery Elementary School
Monday, 1/25: Greenlodge Elementary School
📆 Full agendas and the complete town calendar are here.
📺 Missed a meeting or event? Catch replays at DedhamTV.com.
👀 Looking Ahead
Next week
🕐 Sunday, 11/1: Clocks fall back an hour.
📖 Your Vote is Magic: Monday, 11/2, 6PM at the Main Library. Discover the power (and the magic) of your right to vote. Registration required.
🗳️ State Election: Tuesday, 11/3.
📿 Jump Ring Bracelet Beading Class: Wednesday, 11/4, 6PM at the Main Library, with Sue Underwood of Mystic Moon Beads.
📚 Local Author Book Talk with Janis Robinson Daly: Thursday, 11/5, 6:30PM at the Main Library. She discusses her novel, Under Two Flags. Select Board also meets at 6:30PM.
LATER
🏀 Buddies vs. Badges: Friday, 11/6, 4PM at the Dedham High School gym. The 4th annual game pits Best Buddies against the Dedham Police. Suggested donation is $10 (cash only), and shirts will be sold at the game for $15.
🏒 Dedham Youth Hockey Trivia Night: Friday, 11/6, 7PM at American Legion Dedham. Tables of 10 and individual tickets available. Register.
🐮 Dedham Day: Saturday, 11/7, Barnes Memorial Park.
🥕 Dedham Farmers Market goes indoors. The winter market returns to Dedham Square with live music each week. Saturday 11/14, 10AM–1PM. More winter dates: 12/12, 1/23, 2/20 and 3/20.
🛍️ 43rd Annual DJWC Craft Fair: Saturday, 11/21, 9AM–3PM at Dedham Middle School. 100+ juried crafters, a luncheon starting at 11:30AM, and a crafters' raffle table. Admission is $5 per person; kids under 12 are free. Questions: [email protected].
🔭 Look Up This Week
🌕 Fri 10/23–Sat 10/24: The nearly full moon passes Saturn all night.
🏹 Sun 10/25–Mon 10/26: The Hunter's Moon is full at 12:11AM Monday. It rises around sunset Sunday and lights the whole night.
☄️ Around 11/5: The Southern Taurids peak, with slow, bright meteors and no moonlight in the way.
🪐 Coming up: Mars and Jupiter close in on each other in the pre-dawn sky ahead of a big conjunction on 11/15.
🚗 Beyond Dedham
🍻 Contigofest '26 at Roundhead: Saturday, 10/24, 12PM–10PM. Roundhead turns 4 with a full day at the Powerhouse in Hyde Park. Entry is free, but you'll need the $25 commemorative glass (includes 3 pours) if you're coming for beer. 12–4PM is all ages, with live music, art-making, an empanada-making workshop (sign up at the fest, limited slots), 16+ beers on tap, and three new releases. 4–10PM is 21+.
🎃 Hale-o-ween 2026: Hale's annual kid-friendly Halloween event in Westwood. Saturday, 10/24, 1–3PM and 4–6PM.
🍂 Fall Craft Fair at Crescent Ridge (Sharon): Saturdays, 10/24 and 11/7, 12–3PM at Crescent Ridge Dairy Bar. 30+ vendors, hayrides, face painting, and ice cream.
22 ChatGPT Agents Built for Every Marketing Job
Most marketers use ChatGPT to do general research and then call it an AI strategy. The ones outperforming them are deploying specialized agents built for specific jobs.
We put together 22 plug-and-play ChatGPT marketing agents that handle the work eating your week, each with built-in instructions and structured outputs ready to go in under 5 minutes.
Subscribe to Marketing Against the Grain and get all 22 free.
Inside you'll find:
Competitive intelligence agent that visits competitor websites and builds detailed comparison matrices automatically
Customer feedback analyzer that ranks improvement opportunities by business impact
Social listening specialist that monitors brand mentions and flags reputation risks before they escalate
Campaign optimization agents that handle attribution analysis and surface what is actually driving results
Your competitors are already running agents like these.
Get 22 ChatGPT Marketing Agents free when you subscribe to Marketing Against the Grain today.
💭 Closing thoughts
As always, double-check links before heading out — times and details can change. If you see an error or have something to add, hit reply.
Got this from a friend? Sign up here.
Want to sponsor The Dedham Drop? Get more info here
*Occasionally, I’ll include affiliate links. If you click, I may receive a tiny commission. Most of the time, you’ll receive an offer. Win/Win! These products/services mentioned are ones I believe in.

