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Best events in
Oakham

Events and things to do in Oakham, MA reflect the town's quiet, community-focused character. The historic Oakham Town Center serves as a hub for local gatherings and historical programs. For a wider selection of concerts and dining, residents often travel to nearby Worcester.

The historic Town Center provides a serene backdrop for community life, with activities often centered around the Fobes Memorial Library and the Oakham Town Common.
Annual traditions unite the community, including a town-wide yard sale organized by the Oakham Historical Association and a local Oktoberfest celebration.
Enjoy the rural scenery with wine tastings and local music at Agronomy Farm Vineyard or participate in a charity tournament at Quail Hollow Golf & Country Club.

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AI at Work: Training Session and 25th Anniversary Celebration

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The Barn at Wight Farm

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Mass/CONNECT Conference 2026 - The World Needs Art

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Sturbridge Host Hotel & Conference Center

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Worcester Halloween Singles Mixer 2026

Sat, Oct 17 • 7:00 PM

Worcester, MA

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Speed Dating Ages 50-65 in Worcester, MA at Cocktail Garden & Kitchen primary image

Speed Dating Ages 50-65 in Worcester, MA at Cocktail Garden & Kitchen

Thu, Oct 22 • 7:00 PM

Cocktail Garden & Kitchen

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Boobs Ghouls and Goblins primary image

Boobs Ghouls and Goblins

Sat, Oct 24 • 9:30 PM

Cedar Box Lounge

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Halloween Paranormal Investigation and Dinner at The Publick House Inn! primary image

Halloween Paranormal Investigation and Dinner at The Publick House Inn!

Thu, Oct 29 • 6:00 PM

Publick House Historic Inn

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Wooden Horse: A Tribute to America & Crosby, Stills, Nash & Young + Dinner primary image

Wooden Horse: A Tribute to America & Crosby, Stills, Nash & Young + Dinner

Thu, Oct 29 • 6:00 PM

The Barn at Wight Farm

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The Mitch Chakour Band at the Frontroom primary image

The Mitch Chakour Band at the Frontroom

Fri, Nov 27 • 7:00 PM

WCUW 91.3

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AI at Work: Training Session and 25th Anniversary Celebration primary image

AI at Work: Training Session and 25th Anniversary Celebration

Thursday • 3:00 PM

The Barn at Wight Farm

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Mass/CONNECT Conference 2026 - The World Needs Art primary image

Mass/CONNECT Conference 2026 - The World Needs Art

Sat, Oct 17 • 8:00 AM

Sturbridge Host Hotel & Conference Center

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Worcester Halloween Singles Mixer 2026 primary image

Worcester Halloween Singles Mixer 2026

Sat, Oct 17 • 7:00 PM

Worcester, MA

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Speed Dating Ages 50-65 in Worcester, MA at Cocktail Garden & Kitchen primary image

Speed Dating Ages 50-65 in Worcester, MA at Cocktail Garden & Kitchen

Thu, Oct 22 • 7:00 PM

Cocktail Garden & Kitchen

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Boobs Ghouls and Goblins primary image

Boobs Ghouls and Goblins

Sat, Oct 24 • 9:30 PM

Cedar Box Lounge

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Halloween Paranormal Investigation and Dinner at The Publick House Inn! primary image

Halloween Paranormal Investigation and Dinner at The Publick House Inn!

Thu, Oct 29 • 6:00 PM

Publick House Historic Inn

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Wooden Horse: A Tribute to America & Crosby, Stills, Nash & Young + Dinner primary image

Wooden Horse: A Tribute to America & Crosby, Stills, Nash & Young + Dinner

Thu, Oct 29 • 6:00 PM

The Barn at Wight Farm

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The Mitch Chakour Band at the Frontroom primary image

The Mitch Chakour Band at the Frontroom

Fri, Nov 27 • 7:00 PM

WCUW 91.3

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(ONLINE) Women on the Move with Ann Patchett

Tue, Oct 27 • 11:30 AM EDT

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Fri, Oct 30 • 2:00 PM GMT

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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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Lean Global Connection 2026

Thu, Nov 12 • 2:00 PM UTC

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Washington Crossing the Delaware / The Crossing - Film History Livestream

Sat, Dec 19 • 8:00 PM EST

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HBR Book Webinar: Resilient Optimism

Thursday • 1:00 PM GMT+1

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Coming Together for Multilingual Children with DLD

Thu, Oct 22 • 6:00 PM GMT+2

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Biodiversity Law and Governance Day 2026

Sat, Oct 24 • 11:30 AM GMT+4

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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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Witch hunts and real lives

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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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Thu, Nov 12 • 2:00 PM UTC

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

Washington Crossing the Delaware / The Crossing - Film History Livestream

Sat, Dec 19 • 8:00 PM EST

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Frequently asked questions about Oakham

What are some family-friendly events in Oakham, MA?

Oakham offers several wholesome, family-friendly events throughout the year. The annual G.A.B.B. Golf Tournament at Quail Hollow is a family-oriented charity event. Additionally, the Fobes Memorial Library hosts programs for all ages, and the town-wide yard sale provides a fun outing for the whole family.

Are there free things to do in Oakham?

Yes, there are free activities centered around community and history. The Oakham Historical Museum holds a free open house on the monthly of each month from May through October. Strolling through the historic Oakham Town Center and enjoying the common is another pleasant, cost-free activity.

Where can I find live music events in Oakham?

Agronomy Farm Vineyard is a key spot for enjoying live music in a scenic, countryside setting. While the local scene is intimate, the nearby city of Worcester offers a much wider variety of music venues and concert events for those seeking more frequent performances.

What is there to do for a date night in Oakham?

A great date night idea in Oakham is visiting Agronomy Farm Vineyard for a wine tasting. For dinner and a broader range of entertainment, most couples head to the more extensive restaurant and cultural scene in nearby Worcester.

What kinds of food and drink events are in Oakham?

The local food and drink scene is highlighted by annual celebrations and local producers. The town participates in an annual Oktoberfest, and Agronomy Farm Vineyard offers regular wine tastings. For a full restaurant experience, Worcester provides many more choices.

Are there outdoor events in Oakham?

Yes, Oakham's rural landscape is perfect for outdoor events. The Oakham Historical Association organizes an annual town-wide yard sale, and Quail Hollow Golf & Country Club hosts the G.A.B.B. Golf Tournament. The vineyard also provides a beautiful outdoor setting for its events.

What happens in the Oakham Town Center Historic District?

The Oakham Town Center is the heart of community activity. The area hosts gatherings on the Town Common, while the Fobes Memorial Library and Oakham Historical Museum provide regular programs and events that celebrate the town's culture and history.

Is there a nightlife scene in Oakham?

Oakham is a quiet town with very limited nightlife. An evening event might include local music at Agronomy Farm Vineyard. For bars, clubs, and late-night entertainment, residents typically make the short trip to Worcester.