Restaurants in Chester

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Joe Helbing captained Howlett's tavern for 13 years before deciding to explore a new career path, only to discover he missed the clink of beer glasses and the chatter of happy guests. Having reaffirmed his passion for the restaurant biz, Joe reopened his restaurant, where he continues to serve the original Howlett's memorable menu of steak-house favorites.

Deep in the kitchen, chefs grill a variety of hand-cut steaks, ribs, and fresh seafood dishes. To craft their signature crab cakes, they season fresh lump crab with a savory rémoulade. Come lunchtime, they turn their attention to making thick paninis and hearty burgers and shaking their fists at the relentless midday sun. Guests linger over last sips of cocktails and final bites of housemade pecan pie at tables that speckle the spacious dining room.

3530 Festival Park Plz
Chester,
VA
US

At Don Pepe Mexican Restaurant, an expansive menu of fajitas, burritos, and steaks illustrates the breadth and depth of the Mexican culinary tradition. Nachos in 10 varieties greet diners with juicy morsels of chicken or beef and a crunch that could wake a jet-lagged Rip Van Winkle. Enchiladas team up with tacos or tamales to form hearty combos, or go solo to showcase classic Mexican ingredients such as poblano peppers and green tomatillos. Quesadillas can be stuffed with vegetarian-friendly fillings, such as mushrooms, or meaty delights, such as house-made chorizo. To round out meals, xangos come with a dusting of cinnamon sugar that impresses sweet teeth as much as a coating of edible diamonds.

2102 West Hundred Road
Chester,
VA
US

At Sideline Cafe, the staff works to treat every patron like family—but they don’t want that to scare anyone off. More importantly, the crew draws on nearly two decades in business to forge a diverse menu of homestyle dishes beneath large-screen televisions and a fully stocked bar. Amid wood paneling and sports memorabilia, crispy fried hush puppies and fried okra hint at quick spells in bubbling oil, and steaks and burgers let tables flaunt their strength. While two-handing a burger or juicy sandwich, diners can create new brain wrinkles at weekly trivia nights or channel the emotions of a small-town girl living in a lonely world during weekend karaoke.

10348 Iron Bridge Rd
Chester,
VA
US

A family-owned restaurant for more than 29 years, Klara’s Kitchun was named after the family’s matriarch, Clara Whitt, whose signature recipes inspired a menu of hearty, homestyle dishes. Cozy booths help customers relax and relish the scent of okra, pot roast, and homemade rolls and cornbread. Entrees pair with 20 sides, such as candied yams and fried apples, and homemade coconut cream pie and cherry cobbler beguile sweet teeth. Cooks can also dole out hearty lunch boxes or catered fare for weddings, special events, and Abraham Lincoln look-alike conventions.

11360 Iron Bridge Rd
Chester,
VA
US

Since 1975, The Crazy Greek has loaded customers' bellies with satisfying Italian, Greek, and American dishes. Teeming plates of spaghetti emerge from the kitchen topped with a molten layer of mozzarella cheese, and the chefs stuff pitas with fragrant strips of spit-roasted lamb to create gyro sandwiches. The chefs also bake their own bread and craft their own desserts in-house. The eatery's full bar shakes up specialty libations to sip while watching sports events or knitting circles on the two HDTVs.

14640 Hancock Village Street
Chesterfield,
VA
US

Tropical Smoothie Café's wholesome smoothies are filled to the gills with fresh fruit, juices, yogurt, chocolate, nuts, and healthful supplements, minimizing the crushing guilt of dessert consumption to a soft heartbeat emanating from the floorboards. Puréed potions such as pomegranate plunge (pomegranate, banana, strawberries, and cranberry; $4.79) are stuffed with super fruit, and low-fat options, such as mango magic (mango, pineapples, and non-fat yogurt; $4.29), trick gullible taste buds into believing that they are traversing a candy factory full of whipped-cream lollipops. Supercharged smoothies are stocked with a healthy dose of supplements, such as the kiwi citrus green tea's antioxidant-laden matcha charge or the muscle blaster's whey or soy protein ($4.79 each). Individual supplements can also be added to any other smoothie ($0.79 extra), boosting its magic points by +10.

11513 Busy St
North Chesterfield,
VA
US