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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Events near Oakham

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Haunted Speakeasy Worcester

Tomorrow • 8:00 PM

Creative Hub Worcester

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Speed Dating Ages 50-65 in Worcester, MA at Wormtown Brewery

Tuesday • 6:00 PM

Wormtown Brewery

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UXSYM 2026

Thursday • 8:30 AM

Rubin Campus Center, Worcester Polytechnic Institute

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A Decade of Love

Thu, Nov 12 • 6:00 PM

Polar Park

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American Mahjong Open Play at LK Home & Gifts

Sun, Nov 15 • 6:00 PM

LK Home & Gifts

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14th Annual Gateway Cities Innovation Summit

Wed, Nov 18 • 8:30 AM

The Hogan Campus Center at the College of the Holy Cross

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MOVE Worcester | Pilates. Run. Strength. Yoga.

Sun, Nov 22 • 10:00 AM

Polar Park

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Holiday Candle Workshop

Sun, Nov 29 • 12:00 PM

Hardwick Winery

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Haunted Speakeasy Worcester

Tomorrow • 8:00 PM

Creative Hub Worcester

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Speed Dating Ages 50-65 in Worcester, MA at Wormtown Brewery

Tuesday • 6:00 PM

Wormtown Brewery

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UXSYM 2026

Thursday • 8:30 AM

Rubin Campus Center, Worcester Polytechnic Institute

Check ticket price on event

A Decade of Love

Thu, Nov 12 • 6:00 PM

Polar Park

Check ticket price on event

American Mahjong Open Play at LK Home & Gifts

Sun, Nov 15 • 6:00 PM

LK Home & Gifts

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14th Annual Gateway Cities Innovation Summit

Wed, Nov 18 • 8:30 AM

The Hogan Campus Center at the College of the Holy Cross

Check ticket price on event

MOVE Worcester | Pilates. Run. Strength. Yoga.

Sun, Nov 22 • 10:00 AM

Polar Park

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Holiday Candle Workshop

Sun, Nov 29 • 12:00 PM

Hardwick Winery

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Nearby cities

Boston

49 miles away

Cambridge

48 miles away

Providence

49 miles away

Somerville

48 miles away

Worcester

14 miles away

Newton

43 miles away

Springfield

32 miles away

Brookline

47 miles away

Waltham

41 miles away

Lowell

42 miles away

Nashua

41 miles away

Pawtucket

47 miles away

Lexington

42 miles away

Burlington

43 miles away

Medford

48 miles away

Framingham

32 miles away

Marlborough

26 miles away

Keene

42 miles away

Arlington

46 miles away

Agawam Town

33 miles away

Holyoke

31 miles away

Tariffville

49 miles away

Woburn

47 miles away

Northampton

31 miles away

Manchester

47 miles away

Watertown Town

45 miles away

Westfield

41 miles away

Cranston

48 miles away

Hudson

25 miles away

Hartford

50 miles away

Boston

49 miles away

Cambridge

48 miles away

Providence

49 miles away

Somerville

48 miles away

Worcester

14 miles away

Newton

43 miles away

Springfield

32 miles away

Brookline

47 miles away

Waltham

41 miles away

Lowell

42 miles away

Nashua

41 miles away

Pawtucket

47 miles away

Lexington

42 miles away

Burlington

43 miles away

Medford

48 miles away

Framingham

32 miles away

Marlborough

26 miles away

Keene

42 miles away

Arlington

46 miles away

Agawam Town

33 miles away

Holyoke

31 miles away

Tariffville

49 miles away

Woburn

47 miles away

Northampton

31 miles away

Manchester

47 miles away

Watertown Town

45 miles away

Westfield

41 miles away

Cranston

48 miles away

Hudson

25 miles away

Hartford

50 miles away

Online Events

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OUTSIDER ART: Drawing The Spirit World

Today • 6:30 PM GMT

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Humanitarian Water Engineering Fall 2026

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

Thursday • 1:00 PM GMT

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Managing Your Emotions - Prof Ethan Kross

Tue, Nov 10 • 7:00 PM GMT

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Lean Global Connection 2026

Thu, Nov 12 • 2:00 PM UTC

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REVISED Cottage Food Safety Statewide Online Training

Fri, Nov 13 • 9:00 AM MST

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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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OUTSIDER ART: Drawing The Spirit World

Today • 6:30 PM GMT

Check ticket price on event

Humanitarian Water Engineering Fall 2026

Check ticket price on event

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

Thursday • 1:00 PM GMT

Check ticket price on event

Managing Your Emotions - Prof Ethan Kross

Tue, Nov 10 • 7:00 PM GMT

Check ticket price on event

Lean Global Connection 2026

Thu, Nov 12 • 2:00 PM UTC

Check ticket price on event

REVISED Cottage Food Safety Statewide Online Training

Fri, Nov 13 • 9:00 AM MST

Check ticket price on event

The MI5 Archive: Official Secrets

Fri, Nov 27 • 2:00 PM GMT

Check ticket price on event

Washington Crossing the Delaware / The Crossing - Film History Livestream

Sat, Dec 19 • 8:00 PM EST

Check ticket price on event

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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.

Events near Oakham

Haunted Speakeasy Worcester

Speed Dating Ages 50-65 in Worcester, MA at Wormtown Brewery

UXSYM 2026

A Decade of Love

American Mahjong Open Play at LK Home & Gifts

14th Annual Gateway Cities Innovation Summit

MOVE Worcester | Pilates. Run. Strength. Yoga.

Holiday Candle Workshop

Haunted Speakeasy Worcester

Speed Dating Ages 50-65 in Worcester, MA at Wormtown Brewery

UXSYM 2026

A Decade of Love

American Mahjong Open Play at LK Home & Gifts

14th Annual Gateway Cities Innovation Summit

MOVE Worcester | Pilates. Run. Strength. Yoga.

Holiday Candle Workshop

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Nearby cities

Boston

Cambridge

Providence

Somerville

Worcester

Newton

Springfield

Brookline

Waltham

Lowell

Nashua

Pawtucket

Lexington

Burlington

Medford

Framingham

Marlborough

Keene

Arlington

Agawam Town

Holyoke

Tariffville

Woburn

Northampton

Manchester

Watertown Town

Westfield

Cranston

Hudson

Hartford

Boston

Cambridge

Providence

Somerville

Worcester

Newton

Springfield

Brookline

Waltham

Lowell

Nashua

Pawtucket

Lexington

Burlington

Medford

Framingham

Marlborough

Keene

Arlington

Agawam Town

Holyoke

Tariffville

Woburn

Northampton

Manchester

Watertown Town

Westfield

Cranston

Hudson

Hartford