On a Saturday morning in Norfolk, a couple dozen riders roll down the Elizabeth River Trail with a DJ's beats trailing behind them. The music comes from a boombox, the pace is conversational, and nobody is racing. That scene has repeated most weekends since May 2019, and it will repeat again on Saturday, October 31, 2026, when the LIVE.LIFE.FRESH Boom Box Bike Ride gathers at the Elizabeth River Trail's Trailside Headquarters at the corner of Orapax Street and Raleigh Avenue. Riders meet at 10 a.m.; the group rolls out at 10:30 for a casual cruise through the city's bike lanes and along the trail.
The ride is the work of DJ Bee, a veteran turntablist with more than 28 years of terrestrial radio experience in Hampton Roads. Bee is the founder of Fresh Radio, the online station he launched on October 10, 2010, playing classic and progressive hip-hop, R&B, soul, reggae, funk, disco and boogie, with DJs from around the world around the clock. He also hosts the Fresh Start Morning Show on Norfolk State University's 91.1 FM. In January 2019, he and his wife opened Freshtopia, a record shop and retail space that operates inside the Fresh Radio studio. The shop has been described as one of the few Black-owned brick-and-mortar record stores in the country and was featured in Essence Magazine's list of Black-owned record stores to visit.
The bike ride grew directly out of that storefront. Freshtopia opened on 35th Street in Norfolk's Park Place neighborhood, a stretch that carries the only center-running bike lane in the city and connects to the Elizabeth River Trail. Bee noticed that no Bike Month activities were scheduled for 35th Street in May 2019. So he and his wife called a group of friends who ride, put out a call on Fresh Radio and social media, and met on the first Saturday in May to ride the lanes and the trail. When May ended, they kept going.
"May is Bike Month and we decided to do a weekly bike ride and when the month of May in 2019 ended, we continued," Bee told WTKR. The motivation was partly practical: the shop sat on a street with bike lanes down its center, and the owners wanted to see those lanes used.
The ride largely went dark in 2020, when the pandemic disrupted group gatherings, but it returned in March 2021. By then the weekly ritual had become something more than exercise. Bee has described the rides as a way for people to see parts of the city they might otherwise miss. "When we ride, the Elizabeth River Trail and the bike lanes take you through places of Norfolk you might never have seen before so every new rider is like, 'I didn't know this is back here, this don't look like Norfolk,'" he told WTKR. "So it's good, they get to see the city."
He also frames cycling as a mental reset as much as a physical one. "You start thinking about things. You're being careful and making sure you don't get hit, but you're also coming up with ideas on the way to work and you'll be able to tackle the day a lot better I think, with a clear mind," he said. And on the subject of Bike to Work Day, he was blunt and funny: "Who doesn't want to ride their bike to work? I mean there should be a shower at work if you live too far. It should also be National Shower at Work Day."
The ride's community role has extended beyond Saturday mornings. During the pandemic, Freshtopia kept its doors useful, setting aside three computers with internet service so neighbors could file for unemployment, contact teachers or apply for jobs. Bee and his wife also helped secure a grant that brought bike racks to the block and partnered with city groups to distribute reusable cloth face masks. "I'm just a DJ; that's what I love to do. But my passion has turned into something major that I can help the community with," he told WTKR.
The starting point for the October 31 ride is itself new. The Elizabeth River Trail Foundation opened its first-ever headquarters and visitor center at 715 Orapax Street in the Chelsea District on April 25, 2026, during Celebrate Trails Day, the national Rails to Trails Conservancy celebration. The hub gives trail users a place to start, and thanks to VisitNorfolk and a grant from the Virginia Tourism Corporation, it houses the trail's first bike fleet for rentals. "This is the best way to define the gems of the best that Norfolk has to offer," executive director Kindra Greene said at the opening. "It connects all of our cultural institutions, art, culture and all of the things."
The trail itself has been stitching the city together since 2003, running more than 10.5 miles along Norfolk's working waterfront and connecting 28 neighborhoods, with plans to extend east along the Elizabeth River. The foundation marks its tenth anniversary in November 2026.
For anyone who has never ridden in a group, the Boom Box ride is deliberately low-pressure. It is family-friendly, free and open, and it moves at the speed of conversation rather than a training ride. The route uses the trail and the city's bike lanes, which makes it a practical introduction to navigating Norfolk by bicycle with other people around. Because the ride is led by Freshtopia, riders are advised to follow the shop's channels for last-minute weather changes or cancellations; the ride runs weather permitting.
Riders should plan to arrive at the Trailside Headquarters at Orapax Street and Raleigh Avenue by 10 a.m. on Saturday, October 31, 2026. The group departs at 10:30 and returns within the hour. Bring a bike in working order, and expect music.