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.

Holiday Movie Night – Bel Air

The Armory 37 Main Street, Bel Air, MD, United States

The Annual Holiday Movie Night at the Armory will be held at 7 p.m. with a showing of Brave and pre-show entertainment by the Ryan-Kilcoyne School of Irish Dance at…

Hometown Holidays – Brunswick

Downtown Brunswick 1 W. Potomac Street, Brunswick, MD, United States

Enjoy breakfast with Santa, horse drawn carriage rides, The Brunswick Heritage Museum by candle light and a Children's Holiday Party

Three Saturdays in December – Frederick

Downtown Frederick 10 Church Street, Frederick, MD, United States

Holiday cheer has made its way to Downtown Frederick. Each Saturday in December will feature carriage rides provided by the City of Frederick, hot cocoa & s'mores, live entertainment and more. Over 80 shops, galleries, and restaurants will be open until 9pm. Beat the hustle and bustle of the holiday shopping season and Get It Downtown!

Second Saturday and Art Walk – Cambridge

Downtown Cambridge 400 Race Street, Cambridge, MD, United States

This monthly event in downtown Cambridge features late shopping hours, free gallery receptions, live music, dining specials, and more. Shop and galleries stay open until at least 8pm.

Eleventh Hour – Annapolis

Downtown Annapolis 100 Main Street, Annapolis, MD, United States

Annapolitans and visitors won’t want to miss the three nights of late night shopping and entertainment in downtown Annapolis: Midnight Madness on Thursday, December 4 and 11, and  Eleventh Hour…

Old Fashion Christmas – Elkton

Downtown Elkton 103 North Street, Elkton, MD, United States

Featuring carolers, Elkton High School Jazz Ensemble, Free Clydesdale Horse and Carriage Rides, and holiday treats in all the businesses, and Santa!

Three Saturdays in December – Frederick

Downtown Frederick 10 Church Street, Frederick, MD, United States

Holiday cheer has made its way to Downtown Frederick. Each Saturday in December will feature carriage rides provided by the City of Frederick, hot cocoa & s'mores, live entertainment and more. Over 80 shops, galleries, and restaurants will be open until 9pm. Beat the hustle and bustle of the holiday shopping season and Get It…

New Year’s Eve Ball Drop – Berlin

Downtown Berlin 2 N. Main Street, Berlin, MD, United States

Berlin transforms into a mini Times Square with dancing in the streets, music, fabulous food, refreshments and plenty of entertainment. Count down the New Year with a ball drop at…

Oakland Winter Fest

Oakland, Maryland Oakland, MD

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…

Berlin Spring Celebration

14 South Main Street; Berlin, MD Berlin, MD

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