Maryland is filled with charming downtown areas. Many of them are historic, and best of all, hold enchanting events year-round. These 10 places in particular are worth visiting for their First Fridays, Second Saturdays, Third Thursdays, and more!
- Ellicott City
Facebook / Visit Ellicott City Ellicott City continues to recover from its second infamous flood but many shops have reopened and events have continued. Head here for First Friday and Girl’s Night Out. One of our favorite events is their annual Springfest, featuring live music all weekend long.
- Chestertown
Facebook / Downtown Chestertown Association This quirky town holds an annual Harry Potter themed festival and it’s a must-see. Be sure to also visit regularly for First Friday and Second Saturday.
- Berlin
Facebook / Town of Berlin Maryland We love this town during Christmastime, complete with carriage rides. Be sure to also check out the seasonal farmers markets and outdoor movie nights.
- Frederick
Facebook / Visit Frederick - Maryland This spot also comes to life during the holiday season, with twinkling lights lining Main Street. There’s also often live music in the downtown area and don’t miss out on restaurant week. The eateries here are phenomenal.
- Havre de Grace
Facebook / Explore Havre de Grace Enjoy a variety of family events as well as tasty festivals like the annual Oktoberfest. Want to see something really unique? Check out Havre de Grace’s upcoming Ice Festival!
- St. Michaels
Facebook / Visit St. Michaels, Maryland Christmas in St. Michaels is always a good time, especially when it comes to the parade, complete with llamas. And since this town is waterside, there are plenty of nautical events as well, including skipjack races and more.
- Sykesville
Facebook / Downtown Sykesville Connection Cookie and cocoa crawls, a craft beer festival, and girl’s night out are just a handful of events you can experience in downtown Sykesville. During warmer months, check out the farmers market every Sunday for a variety of local produce and handmade goods.
- Mount Airy
Facebook / Town of Mount Airy Mount Airy features events such as their chocolate crawl, Oktoberfest, and whimsical chalk art competition. Head here to soak in the history and family fun.
- Leonardtown
Facebook / Town of Leonardtown This small town is big on events. Come witness parades and outdoor concerts. And don’t miss out on the annual Earth Day celebration.
- Boonsboro
Facebook / Town of Boonsboro, Maryland Boonsboro Days is a favorite local event. Be sure to also visit this town during summer months for concerts in the park and outdoor movies.
What are your favorite downtown events around Maryland? Let us know below!
Facebook / Visit Ellicott City
Ellicott City continues to recover from its second infamous flood but many shops have reopened and events have continued. Head here for First Friday and Girl’s Night Out. One of our favorite events is their annual Springfest, featuring live music all weekend long.
Facebook / Downtown Chestertown Association
This quirky town holds an annual Harry Potter themed festival and it’s a must-see. Be sure to also visit regularly for First Friday and Second Saturday.
Facebook / Town of Berlin Maryland
We love this town during Christmastime, complete with carriage rides. Be sure to also check out the seasonal farmers markets and outdoor movie nights.
Facebook / Visit Frederick - Maryland
This spot also comes to life during the holiday season, with twinkling lights lining Main Street. There’s also often live music in the downtown area and don’t miss out on restaurant week. The eateries here are phenomenal.
Facebook / Explore Havre de Grace
Enjoy a variety of family events as well as tasty festivals like the annual Oktoberfest. Want to see something really unique? Check out Havre de Grace’s upcoming Ice Festival!
Facebook / Visit St. Michaels, Maryland
Christmas in St. Michaels is always a good time, especially when it comes to the parade, complete with llamas. And since this town is waterside, there are plenty of nautical events as well, including skipjack races and more.
Facebook / Downtown Sykesville Connection
Cookie and cocoa crawls, a craft beer festival, and girl’s night out are just a handful of events you can experience in downtown Sykesville. During warmer months, check out the farmers market every Sunday for a variety of local produce and handmade goods.
Facebook / Town of Mount Airy
Mount Airy features events such as their chocolate crawl, Oktoberfest, and whimsical chalk art competition. Head here to soak in the history and family fun.
Facebook / Town of Leonardtown
This small town is big on events. Come witness parades and outdoor concerts. And don’t miss out on the annual Earth Day celebration.
Facebook / Town of Boonsboro, Maryland
Boonsboro Days is a favorite local event. Be sure to also visit this town during summer months for concerts in the park and outdoor movies.
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