Jesse Oaks might seem like a typical American restaurant, best known for its daily specials and pub-food staples: nachos, burgers, and sweets. Look a little closer, though, and you'll see the chefs putting their own creative spin on tried-and-true classics. Sure, they serve regular nachos, but also Irish nachos, swapping out chips for a base of waffle fries. The burgers are innovative too. The 60/40 burger, for instance, boasts a hybrid patty that's comprised of 60% ground beef and 40% bacon, just like the contents of the best gift baskets. Come dessert, there are deep-fried candy bars and peanut butter cups, coated in tempura batter, along with fried brownie bites served fresh out of the fryer. One final dose of the unexpected? The eatery has six sand volleyball courts—including two inside—and hosts tournaments year-round, frequently for charity.
Inspired by the art-deco elegance of the 1940s, Olive Black Martini Lounge entertains guests with a refined roster of classic cocktails, specialty martinis, and soft lighting. Located less than two miles from the Wisconsin border, mixologists wield jiggers and shakers to conjure potions such as the Dark Secret and Pineapple Upside Cake. Selections of authentic tapas dishes settle stomachs after a few drinks, with bite-sized eats such as cajun bacon-wrapped pork tenderloin or seared shrimp served with fresh mango salsa. Meals end sweetly with such succulent desserts, including the signature salted caramel truffle.
In the heart of Wauconda on the shoreline of Bangs Lake, Docks Bar & Grill offers up sweeping water views along with traditional American grill fare. The menu features Docks’ classic homemade crab cakes garnished with mango-chili sauce, the 10-ounce smoked-bacon-brie burger, and Docks Famous barbecue baby back ribs. To keep up a convivial atmosphere, Docks hosts crowd-drawing events nearly every night, including Monday night football and live music on the weekends. While taking in the laid-back but chic decor, which features black leather booths, dark wood furnishings, and intimate lighting, guests can also enjoy drink specials that change daily. For gatherings or private parties, Docks' has a banquet room that overlooks Bangs lake.
Green to its core, The Irish Mill Inn first opened its doors in the early 1930s. Though its origins aren’t exactly clear, some believe the small, unassuming venue operated as a speakeasy before Prohibition’s end in 1933. No matter the case, today, The Irish Mill Inn legally fills the mugs of regulars and newcomers alike, pouring from a drink selection that includes Irish beers and scotch. The food menu, meanwhile, provides an array of hearty bases, highlighted by such Irish classics as shepherd’s pie and bangers with chips. On Friday and Saturday nights, live bands rock the venue, and on Sundays and Thursdays, patrons can share their own music or odes to green beer during open mic events.
As the sun sets over Antioch every Wednesday night, most people are thinking about going to bed; that’s not the case at Port of Blarney. Instead, a captain is firing up his boat for the weekly sunset cruise, which departs from the eatery’s 8-acre stretch of lakefront property. Free to the first 35 diners who made a reservation, many passengers bring a drink from the restaurant’s bar along for the ride after indulging from a menu loaded with classic American and pub food. Inside the Key West¬–themed dining room or on the freshly planted patio, diners nosh on spicy wings, half-pound Black Angus burgers, pizzas, and sandwiches, such as the Havana Cuban, which tucks slices of pork tenderloin, ham, and pickles into french bread. A regular stream of musicians and other live acts hits the stage at Port of Blarney to keep guests entertained as they eat.
On summer weekends, Port of Blarney’s docks also provide a free boat shuttle to Blarney Island, a bar located 1 mile offshore. Legend has it that entrepreneur and card shark Jack O’Connor won the rights to the bar in the 1900s in an all-or-nothing poker game. The bar's success during the past century inspired the founding of Port of Blarney restaurant to feed guests year-round and to ferry revelers to the lake-bound oasis during warmer months or giant-squid migrations.
Behind a red-brick storefront and striped awning, Viva Le Vine's vintners curate a collection of vintages both affordable and high end, pairing them with cheeses and other finger foods. Wooden racks hoist obsidian bottles of reds and whites, and the wine bar dispenses pours and sampling flights alongside microbrews, seasonal cocktails, and martinis. Cushy, black leather furniture and high-top tables dot the brightly lit interior and an upright piano stands against the wall for impromptu instrumental renditions of Gangsta's Paradise. A painting of colorful donkeys stares down enviously from rich burgundy walls at rich plates of succulent chocolates and naan covered in hearty toppings. The shop hosts live entertainment, numerous tastings, and trivia events throughout the year.