Fun, and unique local events are at the heart of the Main Street experience.

Nowhere else can you find delightful festivals like Colorfest in Thurmont and the Peach Festival in Berlin, quirky events like the Tricycle Races in Cambridge and the Muskrat Celebration in Princess Anne, and classic family-friendly activities such as the New Year’s Eve Ball Drop in Cumberland and Holiday Electric Parade and Tree Lighting in Westminster.

With so many great events taking place throughout the year in Main Streets across the state, chances are you’re just a short drive from being a part of what makes the Main Street experience one-of-a-kind. But remember, when the event ends the fun doesn’t have to! Be sure to stay for the great shopping and dining on Main Street too.

View our annual events calendar.

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February 2017

Oakland Winter Fest

February 25 - February 26
Oakland, Maryland, Oakland, MD + Google Map

The Greater Oakland Business Association's Winter Fest has been rescheduled for February 25 and 26th. There will be an ice sculptor, live carvings, craft and food vendors as well as a book signing, carriage rides, great shopping and dining as well as all museums will be open.  

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April 2017

Berlin Spring Celebration

April 15 @ 10:00 am - 5:00 pm
14 South Main Street; Berlin, MD, Berlin, MD + Google Map

Saturday, April 15th; 10 – 5 pm; Easter related events, vendors, bonnet parade and kids crafts and activities.

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May 2017

Chestertown Tea Party Festival

May 26 - May 28
Chestertown, Md, Chestertown, MD + Google Map

May 26-28, 2017 The Chestertown Tea Party Festival celebrates colonial resistance to British rule with re-enactments, vendors, lectures, wine and craft beer, a raft race, and more. It all takes place on the lovingly preserved 18th century streetscapes of the Historic District and on the Chester River. Come visit this National Historic Landmark town and revel in some revolutionary fun.

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June 2017

Downtown Salisbury Festival

June 2 - June 4

Denton garden gala

June 10 @ 6:00 pm - 9:00 pm
Denton, MD, Denton, MD + Google Map

Downtown Denton Main Street will be hosting their annual Garden Gala.

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$15.00

Taneytown Wine, Brew, Music and Art Fest

June 17 @ 11:00 am - 4:00 pm
Memorial Park, Taneytown, MD + Google Map

Family friendly event with artists and unique crafters, music of all genre along with local wineries and microbreweries.  Free Entrance – Tasting is $15.00 for 10 tickets. Proceeds benefit Habitat for Humanity  

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