Best events in
Sterling

There's no shortage of community-focused events and things to do in Sterling, MA. The town's social rhythm is deeply connected to its agricultural roots and the changing seasons, with a focus on family-friendly and outdoor gatherings. From lively markets on the Town Common to large-scale festivals in the surrounding landscape, activity centers on shared local traditions.

The historic Town Center serves as a hub for community life, hosting the Sterling Street Market on summer mornings and the annual Celebrate Sterling event.
Wachusett Mountain is a key destination for major annual festivals like AppleFest and Oktoberfest, drawing crowds for live music and themed activities.
Family-friendly fun is a staple, with seasonal attractions at Davis Farmland and free summer concerts held in Memorial Park.

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Events near Sterling

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Junk Journal Workshop at SSB Devens

Tomorrow • 6:00 PM

Sterling Street Brewing - Devens Location

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Worcester Halloween Singles Mixer 2026

Saturday • 7:00 PM

Worcester, MA

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Wargasm [VIP Upgrade]

Sunday • 6:30 PM

Palladium

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ServSafe Manager Certification Course & Exam

Monday • 9:00 AM

City of Worcester - Inspectional Services

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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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GENERAL ADMISSION TICKET MA BBTT Skills Expo 2026 Presented by F.W. Webb

Thu, Oct 29 • 9:00 AM

Best Western Royal Plaza Trade Center

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2026 Toys Fore Joy Turkey Shoot at Red Tail Golf Club - SATURDAY

Sat, Nov 14 • 9:30 AM

Red Tail Golf Club

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Christmas NYC BUS TRIP-Benefiting Ahimsa Haven

Sat, Dec 12 • 5:30 AM

Twin City Plaza

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Junk Journal Workshop at SSB Devens

Tomorrow • 6:00 PM

Sterling Street Brewing - Devens Location

Check ticket price on event

Worcester Halloween Singles Mixer 2026

Saturday • 7:00 PM

Worcester, MA

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Wargasm [VIP Upgrade]

Sunday • 6:30 PM

Palladium

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ServSafe Manager Certification Course & Exam

Monday • 9:00 AM

City of Worcester - Inspectional Services

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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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GENERAL ADMISSION TICKET MA BBTT Skills Expo 2026 Presented by F.W. Webb

Thu, Oct 29 • 9:00 AM

Best Western Royal Plaza Trade Center

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2026 Toys Fore Joy Turkey Shoot at Red Tail Golf Club - SATURDAY

Sat, Nov 14 • 9:30 AM

Red Tail Golf Club

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Christmas NYC BUS TRIP-Benefiting Ahimsa Haven

Sat, Dec 12 • 5:30 AM

Twin City Plaza

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Nearby cities

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Quincy

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Online Events

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How To Be Kind To Yourself - Shahroo Izadi

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HBR Book Webinar: Resilient Optimism

Thursday • 1:00 PM GMT+1

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HBR Press Webinar: Resilient Optimism

Thursday • 8:00 AM EDT

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Icons of Conquest: Bayeux Tapestry and Domesday Book

Friday • 2:00 PM GMT+1

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Today's RDH Virtual Dental Continuing Education (CE) Event - Oct. 17, 2026

Saturday • 9:00 AM EDT

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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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Lean Global Connection 2026

Thu, Nov 12 • 2:00 PM UTC

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How To Be Kind To Yourself - Shahroo Izadi

Tomorrow • 7:00 PM GMT+1

Check ticket price on event

HBR Book Webinar: Resilient Optimism

Thursday • 1:00 PM GMT+1

Check ticket price on event

HBR Press Webinar: Resilient Optimism

Thursday • 8:00 AM EDT

Check ticket price on event

Icons of Conquest: Bayeux Tapestry and Domesday Book

Friday • 2:00 PM GMT+1

Check ticket price on event

Today's RDH Virtual Dental Continuing Education (CE) Event - Oct. 17, 2026

Saturday • 9:00 AM EDT

Check ticket price on event

(ONLINE) Women on the Move with Ann Patchett

Tue, Oct 27 • 11:30 AM EDT

Check ticket price on event

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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Frequently asked questions about Sterling

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

Davis Farmland offers seasonal agricultural activities and a splash park for children. The town also hosts the annual Sterling Fair with carnival rides and exhibits, and free band concerts take place in Memorial Park during the summer.

Where can I find live music events in Sterling?

Live music is a major feature at the large festival events hosted at Wachusett Mountain. For a more local setting, Memorial Park holds a summer concert series, and the annual Celebrate Sterling event features performances on Main Street.

Are there food and drink events in the Sterling area?

Many local events highlight food, especially the annual fall festivals at Wachusett Mountain like BBQFest and Oktoberfest. The Sterling Farmers Market and Sterling Street Market also offer local produce and goods from area vendors.

How can I find free things to do in Sterling?

The town offers a free summer concert series with band performances at Memorial Park. Additionally, community gatherings like the annual Sterling Fair and Celebrate Sterling provide free admission to enjoy the atmosphere, though some activities have costs.

Which outdoor events are popular in Sterling?

Sterling specializes in popular outdoor events, from the annual Sterling Fair to seasonal festivals at Wachusett Mountain. The Town Center is also a hub for outdoor activity with its summer markets and the Celebrate Sterling festival.

What is the nightlife like in Sterling?

Sterling's evening scene is generally quiet and community-oriented rather than focused on late-night venues. A nice date night could involve a seasonal dinner at the Chocksett Inn or attending one of the town's free evening summer concerts in Memorial Park.

Does Sterling's Town Center host any recurring events?

Yes, the Town Center is the heart of community activity in Sterling, hosting recurring event series. It is the site of the weekly Sterling Street Market during warmer months and the annual Celebrate Sterling festival.

Can I find markets or fairs with local crafts in Sterling?

Local artisans are often featured at community gatherings in Sterling. The Sterling Street Market is a great place to find local goods, and larger annual events like the Sterling Fair and Celebrate Sterling also showcase area crafters and vendors.

Events near Sterling

Junk Journal Workshop at SSB Devens

Worcester Halloween Singles Mixer 2026

Wargasm [VIP Upgrade]

ServSafe Manager Certification Course & Exam

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

GENERAL ADMISSION TICKET MA BBTT Skills Expo 2026 Presented by F.W. Webb

2026 Toys Fore Joy Turkey Shoot at Red Tail Golf Club - SATURDAY

Christmas NYC BUS TRIP-Benefiting Ahimsa Haven

Junk Journal Workshop at SSB Devens

Worcester Halloween Singles Mixer 2026

Wargasm [VIP Upgrade]

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

GENERAL ADMISSION TICKET MA BBTT Skills Expo 2026 Presented by F.W. Webb

2026 Toys Fore Joy Turkey Shoot at Red Tail Golf Club - SATURDAY

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Nearby cities

Boston

Cambridge

Providence

Somerville

Manchester

Worcester

Brookline

Newton

Salem

Lexington

Springfield

Waltham

Brockton

Lowell

Beverly

Pawtucket

Nashua

Burlington

Haverhill

Framingham

Malden

Lawrence

Quincy

Medford

Watertown Town

Cranston

Keene

Everett

Holyoke

Saugus

Boston

Cambridge

Providence

Somerville

Manchester

Worcester

Brookline

Newton

Salem

Lexington

Springfield

Waltham

Brockton

Lowell

Beverly

Pawtucket

Nashua

Burlington

Haverhill

Framingham

Malden

Lawrence

Quincy

Medford

Watertown Town

Cranston

Keene

Everett

Holyoke

Saugus