Annapolis has a long history of being home to adventure seekers. From swashbuckling pirates to the adventurous nature of Naval and recreational sailors, it only seems natural that a leather brand that identifies with the traveling spirit established its home in downtown Naptown. Hobo bags, wallets and other leather accessories are designed to be a traveler’s closest comrade. As your strolling down Main Street, a welcoming red and tan storefront that sits slightly off the beaten path grabs your attention. Upon entering, the charming smell of leather and wanderlust-infused photographs immediately ignites the travel bug that we all know too well.

Founders Toni and Koren Ray (a mother-daughter team) introduced Hobo in 1991, and has since honored her hallmarks: creativity, originality and quality. After getting her start at the world-renowned Georgetown Leather—known for their fashion-forward designs – Ray stayed true to her roots and opened Hobo’s flagship store here in Annapolis in 2012. The downtown store allows locals and visitors to become acquainted with the Hobo brand. It is a genuine representation of the brand’s DNA with the hope that the ‘Hobo vibe’ and undeniable ‘70s energy is felt by the customers and results a wonderful shopping experience.


With the much anticipated holiday shopping upon us, Hobo is participating in Midnight Madness and partnered with the Historic Annapolis Museum Store to raffle off a few fabulous baskets (go check them out!). There is truly something for everyone at the store. From an artisanal limited-edition collection that features bohemian designs created by tattoo artists Mira Mariah and Theoni Sapounas, to sophisticated and durable passport covers and wallets, this is a one-stop-shop for all those who are playing Santa. The quality leather and timeless designs are the gifts that keep giving. Hobo prides themselves on the fact that their products only get better with the use and wear of each adventure.

This family-owned establishment (now owned by Koren and her husband, David Brewer) could find a home in any major fashion city, but their loyalty is to their heritage. Hobo’s hometown pride goes beyond just a place to set up shop as they’re regularly partnering with organizations such as the Lighthouse Shelter by donating items for auctions and extensive involvement with other community causes.


Although it’s a less known fact that this big-league fashion brand is an Annapolis native, the shop off Main Street takes you on a journey that feels like home.

Be sure to stop in this shopping season to check it out for yourself. And don’t forget to sign up for the loyalty rewards program and birthday discount that’s only available at the Annapolis store!


Images courtesy of Kristin Dyak