May in Maryland: Events, Eats & Excuses to Wear Route One
Spring has sprung — and so has your social calendar.
May is one of the best months to be a Marylander. The weather’s warm but not sweaty, crab season is in full swing, and every weekend comes with a new excuse to get out of the house (and into your favorite Route One fit). Here’s what’s happening across the state this month.
🎨 First Saturdays in Frederick – May 3
Photo credit: Bill Adkins / Downtown Frederick Partnership
Frederick’s downtown comes alive with art, music, and local flavor. Stop by for live performances, boutique sales, and street snacks. It’s basically a spring block party with charm. We recommend bringing a lightweight hoodie — and maybe an empty tote bag for shopping spoils.
🛶 Paddleboarding in Annapolis
Photo credit: Visit Annapolis & Anne Arundel County
Break out the tanks and get on the water! Annapolis offers beautiful paddleboard and kayak rentals along Spa Creek and the Severn. Go solo or with friends — just make sure you're repping a crab tee (or at least a Route One hat, for shade and style).
🍷 Baltimore Wine Village – May 8 to June 1
Photo credit: Wine Village in Baltimore
Set in West Shore Park, this pop-up wine garden is pure Euro-style chill. Sip on slushies, groove to live music, and browse artisan stalls. Pro tip: this is a prime spot for spring selfies, so wear something festive!
🐎 Preakness Stakes – May 18
Photo credit: Associated Press via Getty Images
The second jewel of the Triple Crown belongs to Baltimore, baby. Whether you're tailgating at Pimlico or watching with friends, it’s time to don your boldest Route One apparel. Black-eyed Susans encouraged (both floral and boozy).
🌻 Early Sunflower Blooms
Photo credit: Visit Montgomery
Some farms on the Eastern Shore and in central Maryland begin blooming by late May — and they’re prime for golden-hour content. Bring a blanket, a crabby picnic, and wear something photogenic (like one of our bold patterned tees).
🦀 Every Day Is Crab Day
Photo credit: Patricia Gee for Getty Images
It’s crab season, y’all. Whether you’re cracking claws in your backyard or hitting up your local crabhouse, don’t forget your crabby couture. (Pro tip: Wear dark colors. Crab mallets show no mercy and you're way too Maryland for a bib.)
👕 What Are You Wearing This May?
From festivals to feasts, Route One Apparel has the gear for every Maryland adventure.
Shop our latest arrivals and make May your most Maryland month yet.
#mayinmaryland #routeoneapparel #marylandmade
