High Street Hill Association

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High Street Hill Association The High Street Hill Association brings together residents and property owners in the Pill Hill district of Brookline, Massachusetts

09/13/2026

Neighbors: We hope you had a wonderful summer! HSHA is excited to invite you to our first event of the season, the second annual Olmsted Park Fun Run - a free community event for kids of all ages!

Fun Run
Saturday, September 19th
12:00pm Start (updated from the 1pm Lincoln school email)
Location: At the Olmsted Park footpath, near the intersection of Cumberland Rd. & Pond Ave.

The course will be a 0.7-mile (~1.1 km) counter-clockwise loop around Leverett Pond. After the run, enjoy light refreshments and a chance to connect with fellow neighbors.

Course Flyer Herehttps://mcusercontent.com/ee600975c7fa8d4bf7d550c14/files/4a34d1d2-42e1-b93d-331e-71b34ed78bb8/Fun_Run_Snip.pdf

Rain Date: September 20th

Another successful High St., Hill Association annual meeting as per tradition on the first Monday of May, this time feat...
05/09/2026

Another successful High St., Hill Association annual meeting as per tradition on the first Monday of May, this time featuring a presentation on the redevelopment of the public housing campus at the corner of High and Walnut streets .

Belatedly, our annual caroling on the green. Happy New Year!
01/13/2026

Belatedly, our annual caroling on the green. Happy New Year!

High Street Hill Association Annual Meeting May 2025
05/27/2025

High Street Hill Association Annual Meeting May 2025

Happening now — Greater Point & High Street Hill Association Candidates Night! Still time to come on over to Lincoln Sch...
04/14/2025

Happening now — Greater Point & High Street Hill Association Candidates Night! Still time to come on over to Lincoln School, 6:30-8:30 to hear those running for Brookline Select Board and School Committee. Town Meeting candidates from Precincts 4&5 are also here.

04/11/2025

Hear ye, hear ye: the Greater Point Neighborhood Association and the High Street Hill Assocation proudly present 2025 Candidates Night, Monday, April 14th 6:30-8:30pm in the Lincoln School Cafeteria - 19 Kennard Rd. (In person only)

GPNA & HSHA will once again be jointly hosting a discussion with candidates who will be on the town ballot in the May 6th election.
First up will be those running for Select Board. There are three candidates for one open slot: Liz Linder , Carlos Ridruejo, and Michael Rubenstein.
Next will be candidates for School Committee. There are six candidates and three open spots: Helen Charlupski, Valerie Frias, Akiva Leibowitz, Danna Perry, Logan Potere, and Bob Weintraub.
There will also be an opportunity to meet our Precinct 4 & 5 Town Meeting Member candidates.

The signature gathering of the year —Christmas Eve Caroling on the Green. Happiest of Holidays from the High Street Hill...
12/25/2024

The signature gathering of the year —Christmas Eve Caroling on the Green. Happiest of Holidays from the High Street Hill Association

12/11/2024

It's holiday time and the High Street Hill Association is spreading the good cheer! Two events upcoming to mark your calendars:

Annual Holiday Cookie Swap
Saturday, Dec. 14th
3-5:00pm
Philbrick Green

Please join us for the annual HSHA holiday cookie swap which will be held outdoors at the Philbrick Green. We ask all attendees to bring 2 dozen cookies to swap and a container of your choice to bring back home a variety of cookies. Homemade cookies are preferred. Stay warm by a couple fire pits we’ll have on hand! Hot chocolate and s’more kits will be provided by HSHA. Kids of all ages are welcome. Come swap cookies and make s’mores with neighbors at the HSHA holiday tradition!

Caroling on the Green
Christmas Eve
Dec. 24th
4:45pm
Philbrick Green

The High Street Hill Neighborhood Association is honored to be continuing the beloved annual tradition of neighbors gathering on the Philbrick Green to sing Christmas Carols! LED candles and Christmas song books will be provided.

10/28/2024

Dear neighbors,
As a reminder, our annual parade festivities will be this Thursday. Details below.
🗓️ Date: Thursday, October 31st
⏰ Time: 5:30 PM
📍 Location: Tennis Courts on Hawthorn Road & in front of 40 Hawthorn Road

👻 Families with Kids:

Gather at 5:30 PM: Meet by the tennis courts at Cumberland and Hawthorn to get ready for the spooky parade!
Parade Begins at 5:45 PM: Let’s make some noise as we march down Hawthorn Road! Bring anything that clatters, clangs, or jingles—pots, pans, spoons, or musical instruments—whatever you have on hand!
Trick-or-Treating: The parade will end at the far side of Hawthorn Road, where little ghouls and goblins can head off for some candy-collecting adventures around the neighborhood.
🎉 No Kids? No Problem!

W**e & Pellegrino Party! Join us at 5:30 PM in front of 40 Hawthorn Road to sip, socialize, and celebrate. We’ll have plenty of drinks for everyone—whether you’re marching or just cheering on the parade!
Be Part of the Fun! Bring your own noisemakers or just your lively spirit. Let’s make some noise and cheer on the costumed crowd as they pass by.
✨ Don’t Miss Out!
Whether you’re parading, spectating, or just enjoying a drink with friends, this is a community celebration you won’t want to miss. Come out, get festive, and let’s make this Halloween the best one yet!

We can’t wait to see you there!

Address

Brookline, MA
02445

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