Run4Downtown | 2025 Photos | R4DT | Middletown, New York

What Is the Run 4 Downtown—and Why Piccolo’s, Dave & Anna Madden, and Their Team Matter

Every third Saturday in August, Middletown’s streets fill with runners, walkers, families, and neighbors for the Marshall & Sterling Run 4 Downtown (R4DT)—a four-mile run/walk designed to celebrate community and fuel downtown revitalization. Launched in 2006 by Dave and Anna Madden, the race was born from the couple’s desire to give back to the neighborhood that supported their original café, Something Sweet Dessert Café (now Piccolo Cucina e Vino). Run4Downtown

A fast four miles with a bigger purpose

R4DT is more than a great course and a finish-line party—it’s a catalyst. Since its start, the event has donated over $150,000 to projects that restore and enhance Historic Downtown Middletown, including the creation of Run 4 Downtown Park on North Street, a pocket park that’s become a hub for meetups, music, and race-week festivities. Run4Downtown+1Middletown, NY

Runners get a uniquely Middletown experience: live music on the route, a lively “Taste of the Town/Taste of Middletown” celebration, and a post-race scene that regularly draws big crowds. It’s the kind of small-city magic you feel when local businesses, volunteers, and racers all pull in the same direction. orangerunnersclub.orgWALL Radio

The Piccolo’s connection

If you’ve raced, you’ve probably spotted the Piccolo’s team front and center. Piccolo Cucina e Vino—evolved from the Maddens’ beloved Something Sweet—sits right on North Street and continues the couple’s two-decade tradition of feeding, welcoming, and investing in downtown. Their restaurant transformation kept roots in the city while expanding what they could offer the community—exactly the spirit that powers R4DT. Piccolo Cucina e VinoMapQuest

Dave & Anna Madden: community as a team sport

Dave and Anna didn’t just start a race; they built a platform for civic pride. From establishing team contests like Mickey’s Team Challenge to building partnerships that turn race morning into an all-ages block party, the Maddens and their volunteer crew keep the event focused on connection and momentum for the city core.

That impact shows up in the details runners love: a welcoming four-mile format, a staggered women-then-men start that adds excitement up front, and a finish that flows right into downtown businesses. It’s thoughtful by design—and it keeps dollars, smiles, and foot traffic where Middletown needs them most. RunSignup

Why it matters

R4DT proves a local race can be an engine for renewal. The event funds visible improvements, highlights small businesses, and invites first-time visitors to linger—often discovering a new favorite place for coffee, brunch, or dinner at Piccolo’s or just around the corner. When thousands of people show up to move together and then stick around to eat, listen to music, and shop, downtown wins. Run4Downtown+1

How to be part of it

• Race or walk the 4-miler on the third Saturday in August. If you’re new, grab a friend and enjoy the energy—this is one of the Hudson Valley’s can’t-miss community days. Run4Downtown

• Bring a team for Mickey’s Team Challenge and make it a company, club, or family tradition.

• Plan your post-race at Piccolo Cucina e Vino and neighboring spots—because supporting the businesses that support the race is the whole point. Piccolo Cucina e Vino

Year after year, the Maddens and their crew remind us that a great local race doesn’t end at the finish line—it starts conversations, starts traditions, and helps a city keep moving forward. That’s the Run 4 Downtown.