Things to Do in Forest Park

What looks like a crimson-hulled pirate ship glides into view from behind Shedd Aquarium. The wind picks up, surging into the schooner's 77-foot gaff-rigged topsails and speeding the vessel along Lake Shore Drive at 10 knots. Those on shore can just make out the boat's name, Red Witch, and what appear to be passengers raising a drink to the Chicago skyline.

Docked in Burnham Harbor, the Red Witch tall ship is one three vessels in Tall Ship Adventures of Chicago's fleet. Designed by naval architect John G. Alden and named after the book Wake of the Red Witch—the same story that inspired the film starring John Wayne and Gail Russell—the Coast Guard–licensed ship accommodates up to 49 passengers within its mahogany-over-oak frame. Having sailed waters off Maui and San Diego, the boat is now under the stewardship of Captain Andrew Sadock and his crew, which leads tour cruises, coordinates charter adventures, and autographs cannonballs for each passenger.

In addition to being a current member of the American Sail Training Association, the Red Witch finished among the finalists for Best Boat/Cruise Service Provider in the 2010 Illinois Meetings + Events Readers' Choice Best of Awards.

With a fleet of futuristic segways and classic beach-cruiser bicycles, Bike and Roll Chicago outfits travelers with wheeled transportation to explore the city's paved surfaces. Tour guides lead groups through Millennium Park and along the lakefront to catch the skyline when illuminated by sunrises or backlit by one of Chicago's many moons. Misty Lake Michigan breezes ruffle riders' hair peeking through helmets as they pass by sailboats swaying lazily in the harbors and fishermen casting lines for trout and perch. Bike and Roll Chicago designs routes around classic architectural landmarks such as the Shedd Aquarium and Field Museum as well as popular neighborhoods home to a number of restaurants and art festivals.

Gliding through parks and weaving between runners on the lakefront path, segway-riding guides from Signature Segway Adventures keep guests in the know, offering up fun facts about the city and its origins. During tours, they highlight architectural sights, scenic views, and landmarks such as Buckingham Fountain, Navy Pier, and the Shedd Aquarium. Before hopping aboard a self-balancing vehicle, guests take part in an instructional course so they will feel confident and not try to bring their own training wheels from home.

Skydeck Chicago whisks visitors up to the 103rd floor of Willis Tower (formerly the Sears Tower), the tallest building in the Western Hemisphere, for incredible views from 1,353 feet above the city. On the way up, interactive touchscreens and a nine-minute movie about Chicago architecture fill noggins with cloud-scratching trivia and inside info about the historic tower. From the deck, ocular orbs can spy city landmarks such as Soldier Field, the Shedd Aquarium, and the John Hancock Center. Far-sighted pupils can glimpse up to four states or spot sailboats playing badminton near the marina on Lake Michigan. The Ledge—a transparent glass box that extends more than four feet from the tower—offers brave visitors unobstructed views of the city streets directly below, as well as the spine-shivering sensation of walking on air. Visitors descend back to earth armed with unique snapshots of magnificent views, renewed appreciation for the building's 80 miles of elevator cable, and any loose pieces of masonry they pry off the building’s exterior.

A 30-foot sailboat floats across Lake Michigan. It churns through water twinkling with reflections of moonlight, stars, and the Chicago skyline. Suddenly, fireworks shoot into the air, painting the sky above Navy Pier in blooms of red and blue. The USCG–licensed and certified captains at 3rd Coast Cruising create moments like these during private charters and sightseeing tours. They also spend their days leading hands-on lessons that let sailors discover keelboarding or tackle more advanced conditions such as heavy-weather sailing. Launching from the giant wine bottles in DuSable Harbor, 3rd Coast Cruising's fleet also beckons potential captains to compete in sailboat races.

On Wednesday, October 3, independent distillers set up shop at the Warehouse at Carmichael's Chicago Steak House to display and sample their small-batch, artisanal wares for the second annual Independent Spirits Expo. The exhibitors come from all over the country, from Breckenridge Distillery in the Rockies to Ravenswood’s own Koval. Koval will showcase their smooth and organic spirits, including single-barrel oat and millet whiskeys, New Holland—taking a break from beer brewing— will also show off their small-batch whiskeys, and Templeton Rye struts its stuff with its eponymous spirit.