Wednesday, August 27, 2025 5:00 PM by Chesapeake Convention & Visitors Bureau
September in Chesapeake is all about bold flavors, fresh finds, and experiences worth savoring. From craft breweries and bustling farmers' markets to charming farms celebrating the harvest season, Chesapeake’s culinary scene offers something delicious for everyone.
There’s no better time to explore the Chesapeake Ale Trail than in September. Breweries like The Garage Brewery, Big Ugly Brewing, Studly Brewing, and Wasserhund Brewing each bring their own personality to the scene, with seasonal pours, creative flavors, and welcoming atmospheres. From outdoor patios and food trucks to special fall menus and community events, these spots are perfect places to sip, savor, and celebrate Chesapeake’s craft beer culture.
Harvest season shines at Chesapeake’s weekly farmers markets. On Wednesdays and Saturdays at Chesapeake City Park, and daily at Hickory Ridge Farm, you’ll find tables overflowing with grass-fed meats, fresh-cut flowers, herbs, seasonal produce, farm-fresh eggs, and homemade baked goods. It’s farm-to-table at its finest.
Chesapeake’s charming farms come alive in September with pick-your-own pumpkins, hayrides, colorful chrysanthemums, corn mazes, and fresh fall produce. Families will love indulging in homemade ice cream at spots like Irwin’s Fountain or Sundae Scoop, where every scoop is made fresh daily.
Of course, September is also blue crab season in Chesapeake. At Wicker’s Crab Pot Seafood, owner Ray Wicker pulls crabs straight from the Elizabeth River, ensuring you get the freshest catch possible. And if you’re craving a night of fine dining, places like Luce Secondo and The Butcher’s Son round out the city’s diverse dining scene with chef-led menus and elevated flavors.
If you’re craving comfort food with bold flavor, Johnson’s BBQ is a Chesapeake staple. Pitmaster Dan Johnson—five-time winner of Best Ribs in America—slow-smokes his meats to perfection, serving up barbecue that’s as authentic as it gets. For something with island flair, head to Cutlass Grille, where authentic Jamaican dishes like jerk chicken, curried goat, and oxtails bring a taste of the Caribbean right to your plate. And for a rich mix of spices and aromas, Rasoi IV Indian Kitchen delivers with fragrant biryanis, savory curries, and traditional tandoori favorites, all served with warmth and care.
Together, these local favorites showcase the incredible diversity of Chesapeake’s dining scene.
Chesapeake’s culinary story isn’t complete without its beloved mom-and-pop restaurants, where local flavor and hospitality shine. Hotrodders Café, recently featured on America’s Best Restaurants, is known for hearty comfort food and a nostalgic car-themed vibe that makes every visit memorable. Over in Great Bridge, the Sunrise Breakfast Shoppe has been serving the community since 1995, earning loyal fans with generous plates and a true neighborhood feel. To capture the Western Branch spirit, stop by Point Break Café, a cozy spot where locals gather for homestyle meals and friendly service. These small, family-run eateries are the heart of Chesapeake’s food scene—offering the kind of authenticity you can’t find anywhere else.
As the official Destination Marketing Organization (DMO), our mission is to promote and market Chesapeake, VA as a premier visitor and convention meeting destination for the purpose of positively affecting the city's economy.
