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Best events in
Medway

While Medway maintains a quiet, small-town charm, there's a consistent calendar of community events and things to do in Medway, MA. Social life often revolves around family-friendly gatherings at public spaces like Choate Park and the Medway Public Library. For a broader range of entertainment, residents frequently visit nearby towns like Franklin.

The town's social rhythm is centered in Medway Village, where community events often take place at Choate Park or the Thayer Homestead.
Live music has a home at Mickey Cassidy's, a local Irish pub that hosts performances on weekends.
Nearby Franklin expands the possibilities with theater productions at THE BLACK BOX and acoustic sets at the Circle of Friends Coffeehouse.

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Rivers Symphony Orchestra — Mozart & Tchaikovsky

Today • 7:00 PM

Needham Town Hall

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Kerr Smith (8:00pm) primary image

Kerr Smith (8:00pm)

Monday • 8:00 PM

An Unlikely Story

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Joanne Chang presents "The Joy of Cookies"

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MassBay Community College Wellesley Hills Campus

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2026 Champions of the Blackstone Awards Reception

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Six String Grill & Stage

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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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Boston Speed Dating for Singles Age 24-39 ♥ Massachusetts at P.F. Changs - Natick Mall primary image

Boston Speed Dating for Singles Age 24-39 ♥ Massachusetts at P.F. Changs - Natick Mall

Thu, Dec 10 • 7:00 PM

P.F. Changs - Natick Mall

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Rivers Symphony Orchestra — Mozart & Tchaikovsky primary image

Rivers Symphony Orchestra — Mozart & Tchaikovsky

Today • 7:00 PM

Needham Town Hall

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Kerr Smith (8:00pm) primary image

Kerr Smith (8:00pm)

Monday • 8:00 PM

An Unlikely Story

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Joanne Chang presents "The Joy of Cookies" primary image

Joanne Chang presents "The Joy of Cookies"

Tuesday • 7:00 PM

MassBay Community College Wellesley Hills Campus

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2026 Champions of the Blackstone Awards Reception primary image

2026 Champions of the Blackstone Awards Reception

Fri, Nov 13 • 5:30 PM

The Lodge at Diamond Hill

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STRUCK OUT CANCER primary image

STRUCK OUT CANCER

Sat, Nov 14 • 2:00 PM

Six String Grill & Stage

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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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Boston Speed Dating for Singles Age 24-39 ♥ Massachusetts at P.F. Changs - Natick Mall primary image

Boston Speed Dating for Singles Age 24-39 ♥ Massachusetts at P.F. Changs - Natick Mall

Thu, Dec 10 • 7:00 PM

P.F. Changs - Natick Mall

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Wednesday • 7:30 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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This Little World: a New History of Tudor and Stuart England primary image

This Little World: a New History of Tudor and Stuart England

Wednesday • 7:30 PM GMT

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Lean Global Connection 2026 primary image

Lean Global Connection 2026

Thursday • 2:00 PM UTC

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The Walrus Talks at Home: Canada After America

Thursday • 7:00 PM EST

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Physicians Financial Wellness Conference 2026 primary image

Physicians Financial Wellness Conference 2026

Sat, Nov 14 • 1:00 PM EST

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SVPG Product Masterclass - Nov 16-18, 2026 primary image

SVPG Product Masterclass - Nov 16-18, 2026

Mon, Nov 16 • 12:00 PM GMT

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HBR Press Webinar: Unspeakable primary image

HBR Press Webinar: Unspeakable

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Washington Crossing the Delaware / The Crossing - Film History Livestream primary image

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Frequently asked questions about Medway

What are some family-friendly things to do in Medway?

Choate Park is the center for many family-friendly activities in Medway. The park hosts annual traditions like the Pumpkin Walk and Celebrate Medway Day. Additionally, the Medway Public Library offers regular programs and workshops for all ages.

Where can I find live music events near Medway?

Mickey Cassidy's is a go-to spot for live music within Medway itself. For a dedicated performance venue, nearby Franklin offers acoustic shows at the Circle of Friends Coffeehouse and varied musical acts at THE BLACK BOX.

Are there popular outdoor events in the Medway area?

Yes, Medway hosts several well-attended outdoor community events. Celebrate Medway Day is a major annual festival held each July at Choate Park. The park is also home to the weekly Medway Farmers Market from summer through autumn.

What's the nightlife like for a date night in Medway?

Medway's nightlife is relaxed, centered on casual spots like Mickey Cassidy's. For a dedicated show or a wider variety of atmospheres, many people head to the Franklin Cultural District for dinner and a performance at a local venue.

Can you recommend any food-focused events in the area?

The annual FarmFest at Medway Community Farm is a great local food event. For fresh goods, the Medway Farmers Market runs weekly at Choate Park during the warmer months. These gatherings celebrate the region's agricultural community.

How can I find free events to attend in Medway?

Many free community events take place in Medway's public spaces. Check for programs at the Medway Public Library or outdoor gatherings at Choate Park. The Concerts on the Common series in nearby Franklin is also a popular free option.

Which neighborhood is best for finding community events in Medway?

Medway Village is the primary hub for local community events. This central area contains key venues like Choate Park and the Thayer Homestead. These locations frequently host the town's seasonal festivals and gatherings throughout the year.

What kind of art and culture events can be found near Medway?

The area offers a solid mix of cultural events, especially in nearby towns. Franklin hosts theater at THE BLACK BOX and folk music at Circle of Friends Coffeehouse. For crafts, the Holliston Annual Harvest Fair is a well-known regional event.