Amber Flanagan's grandparents moved to Milwaukee from Mississippi in the 1960s, bringing with them their culinary heritage and their firm belief in the importance of good eating. Today, Amber carries on their passion for gastronomical traditions by leading walking food tours of the Silver City District and the Historic Third Ward. Milwaukee’s history as a hub for immigrants from all over the world is reflected in the city's diverse ecosystem of restaurants: tours may bounce between Vietnamese, Peruvian, Thai, and Mexican cuisines on their journey. Some restaurant outings incorporate cooking demonstrations, which could otherwise only be glimpsed after donning an elaborate busboy disguise.
Lake Geneva Canopy Tours elevates tree trekkers 10–75 feet above the 100-acre park to zip along an aerial route surrounded by wildlife, mature forest, and tranquil trails. After gearing up, crews practice zipline techniques a few feet above the ground under the watchful eye of guides and judgmental eagles before implementing their recently honed skills on the canopy course. Nine ziplines navigate patrons across the park along with 18 platforms, five SkyBridges, three tree-based spiral stairways, and a double-helix stairway wrapped around an ash tree that holds the genetic code of Tarzan. Upon reuniting with terra firma, customers conclude their 2.5-hour eco adventure by gearing down and penning thank-you notes to hawks encountered on the expedition. Lake Geneva Canopy Tours begins its daily sessions at 8 a.m. and sends its last group skyward at 3 p.m.
Chuckleberry Farm & Winery invites guests to sample its diverse assortment of wines crafted with blackberry, blueberry, peach, pomegranate, and other delectable fruits, clearing palates with its own homemade jam and jellies. Sniff and sip 14 specialty table wines, with flavors ranging from cherry to elderberry. Tastings harmonize with complimentary cheese, crackers, and a slew of jellies and jams. Following sipping sessions, tasters receive souvenir glasses embellished with the winery's moniker, as well as a take-home bottle of wine handpicked by Chuckleberry's vintners and a Japanese wine-drinking robot. Should the tour's palate-cleansing comestibles catch tongues' attention, Chuckleberry Farm & Winery also stocks pantries with a mélange of full-bodied jellies ($5) and jams ($3.50).
The casual dining room of Grande Lettys transports patrons to the heart of Mexico, surrounding them in painted murals depicting Mexican streets. There's just one more step needed to complete the teleportation: a bite of freshly made guacamole or a housemade tamale. And the eatery's enticing dinner or lunch plates deliver. Chefs cook enchiladas, burritos, and tacos with a choice of fillings, such as steak or a mixture of beans and cheese—which dexterous diners can use to make a sculpture of Pancho Villa. After meals, patrons aged 21 or older can stick around and play video casino games. Insider tip: order a container of a favorite salsa to take home.
The staff at 2K Adventure Gear lures explorers into its storefront with apparel, equipment, and accessories for warm- and cold-weather excursions, and helps keep like minds together by organizing a variety of fun, rough-and-tumble outdoor events. A selection of kayaks, paddles, and life jackets outfit aquatic travelers; snowshoes give trekkers the surefootedness of a mountain goat and the problem-solving savvy of a lab rat with a degree in public relations. Clients can load up backpacks and venture forth on one of the company’s weekly paddling events, held at sites around the Midwest. Beginners can take advantage of lessons that accommodate no more than 12 students, and more practiced paddlers can take group trips to Wisconsin, central France, or a whale’s dreamscape.
All Community Events gathers together athletes of all stripes to set off on brisk, well-organized outdoor runs. In the one-mile Run the Pier jaunt, sprinters can goggle at the skyscrapers surrounding Navy Pier, dash beneath its towering ferris wheel, and reach underneath the pier to grab fistfuls of the cotton candy keeping it afloat before finishing through its welcoming arch. The World's Largest Corn Maze Run/Walk weaves through five kilometers of paths that wind through a dense cornfield, while a pair of Turkey Trots let exercise-hounds burn off calories in advance of the day's traditional feast. Though its exact date will be pinned down as the event draws closer, the Chi Town Half Marathon pits runners against 13.1 miles of verdant north-side terrain. The challenging but beginner-friendly race's March date places it well before most of the year's other major races, and provides a compelling reason to step outside during the dark, werewolf-riddled chill of winter.