The Wine Festival
Hundreds of people will taste our neighborhood's homemade wine, listen to live music and shop with local arts/craft vendors. Food and beer from local eateries and breweries are also available.
This year’s event was April 26th . Next year’s date is not set yet.
The Basement Bar Tour
Come on out and see how Highlandtown entertains! In the past, folks here created elaborate club basements to entertain their family and friends. These days anything goes...from kegerators, to tricked-out game rooms to the good old fashioned kitchen gathering, so join us on our home tour and see these amazing spaces!
The date is not settled yet, but learn more.
Blockenstein
A Monster-sized community yard sale. Blockenstein brings neighbors together to get to know one another with an eye toward creating a safer community as well as providing the opportunity for local residents to sell the extra items that have been accumulating in closets and basements for too long. Any resident with a Highlandtown address is invited to set up a table with yard sale items absolutely free of charge.
See recap for 2026 Blockenstein. 2027 Blockenstein is our 20th Anniversary and is schedules for
The Crab Feast
Crabs… Drinks… Food… Music… awesome neighbors,
It doesn’t get any better than this. Date not set yet.
Jingle & Mingle
Our annual end-of-year get together.
2025 Photos