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Best events in
Holliston

Shaped by historic mill spaces and quiet town greens, the community calendar brings together local events and things to do in Holliston, MA. Washington Street forms the walkable backbone of town, linking historic stores with gathering spots along the Upper Charles Rail Trail. The historic Holliston Mill and Asa Whiting House host recurring community gatherings that define the town's welcoming pace.

Along the Upper Charles Rail Trail, Blair Square serves as a central hub for free outdoor music gatherings and town celebrations.
At The Holliston Mill, artists' lofts host open studio sessions alongside the weekly Holliston Farmers Market.
The Holliston Historical Society on Washington Street hosts annual community traditions, including the Harvest Fair and Oktoberfest.

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OFFSITE: The Fight or Flight Tour with Jeff Kinney (11am Show)

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2026 Boston Symposium on Organic and Bioorganic Chemistry

Fri, Oct 23 • 8:15 AM

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ACOTAR 6 Midnight Release Party

Mon, Oct 26 • 9:00 PM

Wojcik's Farm

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Excellence In Construction Awards Dinner 2026

Thu, Nov 5 • 6:00 PM

Four Points by Sheraton Norwood

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2026 MIT Sloan CFO Summit

Thu, Nov 19 • 7:30 AM

Boston Marriott Newton

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Barcelona Guitar Trio and Dance

Fri, Nov 20 • 8:00 PM

Jordan Hall

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Speed Dating Beyond Small Talk | Boston (Natick) Speed Dating | Tantra Speed Date® primary image

Speed Dating Beyond Small Talk | Boston (Natick) Speed Dating | Tantra Speed Date®

Sunday • 2:30 PM

Common Street Spiritual Center

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2026 MASS Self-Advocacy Conference primary image

2026 MASS Self-Advocacy Conference

Norwood Conference Center at the Four Points by Sheraton Norwood

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OFFSITE: The Fight or Flight Tour with Jeff Kinney (11am Show) primary image

OFFSITE: The Fight or Flight Tour with Jeff Kinney (11am Show)

Sun, Oct 18 • 11:00 AM

King Philip Regional High School

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2026 Boston Symposium on Organic and Bioorganic Chemistry primary image

2026 Boston Symposium on Organic and Bioorganic Chemistry

Fri, Oct 23 • 8:15 AM

Alkermes, Inc.

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ACOTAR 6 Midnight Release Party primary image

ACOTAR 6 Midnight Release Party

Mon, Oct 26 • 9:00 PM

Wojcik's Farm

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Excellence In Construction Awards Dinner 2026 primary image

Excellence In Construction Awards Dinner 2026

Thu, Nov 5 • 6:00 PM

Four Points by Sheraton Norwood

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2026 MIT Sloan CFO Summit primary image

2026 MIT Sloan CFO Summit

Thu, Nov 19 • 7:30 AM

Boston Marriott Newton

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Barcelona Guitar Trio and Dance primary image

Barcelona Guitar Trio and Dance

Fri, Nov 20 • 8:00 PM

Jordan Hall

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47 miles away

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20 miles away

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Brockton

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Pawtucket

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Nashua

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Plymouth

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Haverhill

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Burlington

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Warwick

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Framingham

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Malden

25 miles away

Quincy

21 miles away

Newport

49 miles away

Cranston

30 miles away

Medford

22 miles away

Lawrence

37 miles away

Watertown Town

18 miles away

South Duxbury

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Thu, Oct 15 • 1:00 PM GMT+1

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(ONLINE) Women on the Move with Ann Patchett

Tue, Oct 27 • 11:30 AM EDT

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No Title, No Permission, No Problem: Harnessing the Power of Influence

Thu, Nov 5 • 1:00 PM GMT

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The MI5 Archive: Official Secrets

Fri, Nov 27 • 2:00 PM GMT

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Washington Crossing the Delaware / The Crossing - Film History Livestream

Sat, Dec 19 • 8:00 PM EST

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AI Animation Studio: Create Kids' Cartoons

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HBR Press Webinar: Resilient Optimism primary image

HBR Press Webinar: Resilient Optimism

Thu, Oct 15 • 8:00 AM EDT

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HBR Book Webinar: Resilient Optimism primary image

HBR Book Webinar: Resilient Optimism

Thu, Oct 15 • 1:00 PM GMT+1

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Coming Together for Multilingual Children with DLD primary image

Coming Together for Multilingual Children with DLD

Thu, Oct 22 • 6:00 PM GMT+2

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(ONLINE) Women on the Move with Ann Patchett primary image

(ONLINE) Women on the Move with Ann Patchett

Tue, Oct 27 • 11:30 AM EDT

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No Title, No Permission, No Problem: Harnessing the Power of Influence

Thu, Nov 5 • 1:00 PM GMT

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The MI5 Archive: Official Secrets primary image

The MI5 Archive: Official Secrets

Fri, Nov 27 • 2:00 PM GMT

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Washington Crossing the Delaware / The Crossing - Film History Livestream

Sat, Dec 19 • 8:00 PM EST

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Frequently asked questions about Holliston

Where can families find free events in Holliston, MA?

Blair Square offers accessible family events, free concerts, and outdoor space right along the Upper Charles Rail Trail. The central plaza hosts a free seasonal concert series alongside town holiday celebrations. Stoddard Park also provides open lawn space for recurring outdoor music gatherings that draw local families.

What are popular date night ideas in Holliston, MA?

Pairing a casual dinner at Casey's Pub with an evening stroll along the Upper Charles Rail Trail creates a relaxed local outing. Located in the historic Mudville neighborhood, the pub offers a laid-back setting for conversations. Golf enthusiasts can also head to Pinecrest Golf Club for an afternoon round followed by dinner at its on-site restaurant.

Which locations host live music events in Holliston, MA?

Blair Square and Stoddard Park serve as the primary venues for seasonal live music events and community band concerts. The weekly market at the local mill features live musical acts alongside regional food vendors. Historic outdoor spaces across town regularly showcase local performers during open-air gatherings.

How can visitors experience art events in Holliston, MA?

The Holliston Mill on Water Street is the town's premier center for local art events and creative gatherings. The historic mill features working artists' lofts that host periodic open studio sessions. Visitors can meet local craftspeople, view original artwork, and browse artisan vendor stalls during seasonal town markets.

Where are the best spots for food and drink events in Holliston, MA?

Out Post Farm provides memorable food events with its bakery and outdoor smoker nights in an authentic agricultural setting. The farm stand hosts weekly barbecue gatherings featuring smoked meats and fresh goods. For local market fare, the weekly Holliston Farmers Market brings local food trucks and craft beverages to The Holliston Mill.

What historic community traditions happen in Holliston, MA?

The Holliston Historical Society hosts classic town gatherings on Washington Street inside the historic Asa Whiting House and Barn. Annual traditions include the Harvest Fair featuring New England crafts, an autumn Oktoberfest, and a classic car show. The downtown area also holds an annual Holiday Stroll with a trolley connecting local shops.

Are there outdoor events available along the Upper Charles Rail Trail?

The Upper Charles Rail Trail connects several key community gathering spots, making it ideal for outdoor fitness and community activities. Blair Square sits directly on the trail and hosts outdoor performances and seasonal festivals. Downtown Washington Street sits steps away, allowing easy access to shops, cafes, and local gathering places.

Is there any nightlife in Holliston, MA?

Nightlife in town is quiet and community-focused, centered around friendly neighborhood hubs rather than late-night dance clubs. Casey's Pub in Mudville offers a cozy setting for evening drinks and conversation with long-time residents. Local dining spots in downtown Washington Street provide relaxed options for evening dinners and low-key social gatherings.