Exploring the Hood- Highlandtown


Three months ago I moved into a new to me neighborhood in Baltimore, Highlandtown. I have always lived within a few blocks from the Inner Harbor and this is about a 10 minute drive. For those not familiar with Highlandtown- its East of Patterson Park and just over Eastern Ave from Canton. It’s quiet, artsy, there’s plenty of parking and Patterson Park might as well be its backyard. 

When my friend Lauren, another Highlandtown resident, suggested we take a day to explore the neighborhood I was 100% in. On Saturday we spent six hours bopping around our neighborhood popping into art studios, bars and restaurants. I learned so much about our little piece of Baltimore and can’t believe it took us this long to explore! 

Here’s what we did/where we went/what we ate/what we saw:

Stop 1: DiPasquale’s


We started the crawl at 1pm and needed food to fuel our journey. DiPasquale’s is an authentic Italian market with a deli counter, pastas and jars of sauce for purchase and a freezer section filled with every pasta and soup you can imagine. I wish I could bottle the smell and share it with you all. So yummy. 

Stop 2: Highlandtown Gallery & Magnolia Designs


So many beautiful pieces that I would love to fill our home with someday…when we have more money! In the meantime the Highlandtown puzzle and coffee mug are more budget friendly and two items I have my eye on. 

Stop 3: Night Owl Gallery


The Night Owl Gallery was tiny but so cute and we were able to snag the bumper sticker I’ve had my eye on for weeks now. YOU’RE NOT IN CANTON ANYMORE….THIS IS HIGHLANDTOWN. 

Stop 4: Baltimore in a Box


We tried to stop in one of my favorite shops ever- Baltimore in a Box but they were closed. Another time!

Stop 5: Rooftop Hots


 It might be the tallest single standing building in our neighborhood and kind of sticks out at you. The first floor is a market with fresh fruit and vegetables that the owners and farmers grow on the roof of the building! They also have a CSA service which sounds perfect in the spring and summer! On the day of our crawl they had limited produce since its the dead of winter here in Maryland but they had the cutest little spider plants. 

Stop 6: Venice Tavern


Venice Tavern is the epitome of an old Highlandtown dive bar. They only take cash, there’s a pool table in the corner and the folks inside are all very much part of the local crowd. I loved it. 

Stop 7: Filippos


Filippos is a bar and pizza shop with the most amazing smelling pizza. We didn’t have a chance to grab a slice but I will absolutely be back! We got beer and enjoyed the sofas next to the windows so we could people watch to our hearts content.

Stop 8: Laughing Pint


Laughing Pint has been on our list for three months to check out because we drive by every day! They have a small bar,  a few booths to eat in, local artwork on the walls, pool tables and a shuffleboard table! I may or may not have lost terribly at shuffle board, but I had so much fun and that’s what matters right?

Stop 9: Y:ART


Y:ART is a HUGE and gorgeous art gallery on Gough Street. We were wandering through their event space when Julie, the owner, came over to chat. We learned so much about the gallery, Julie and all of the artists featured and I never wanted to leave. She was so sweet and the artwork was stunning. 

Stop 10: Snake Hill


The last stop on our Highlandtown tour was Snake Hill which is also the only place I had been to prior to Saturday. We eat there often, love the atmostphere and are friends with the staff now. It was the best place to grab dinner and end the day. 

In one day I saw so much of my new neighborhood and think that Lauren and I will do a few more of these in various neighborhoods. Anyone wanna come with? 

Share:Share on FacebookTweet about this on TwitterPin on PinterestEmail to someone
  • http://kyleandjensmith.blogspot.com/ Jen

    It’s so fun to explore when you move to a new area! It seems like you are settling in nicely. :)

  • rosemary k

    ooh i love dipasquales – when i was a dog walker i used to stop there for lunch all the time. it’s seriously so good!

  • http://www.thefreeandwildblog.com Annie

    Sounds like the BEST day! I love that you got to check out so many different places…I am definitely going to need to check out Rooftop Hots because fresh fruits and veggies? YES PLEASE.

  • http://ohhey-ilikethat.com Lauren

    Omg I’m OBSESSED with DiPasquales! The best best BEST meatball sub I’ve ever had!

  • http://totravelandbeyond.com/ Macy Volpe

    DiPasquale’s is SO good!! We went there almost daily when our office first moved to Highlandtown, now we limit ourselves a little more. Those meatball subs are the BEST. You visited so many cool places, I need to try some of these bars! I have a friend that lives above Laughing Pint!