Milwaukee
Historic Milwaukee Inc. Volunteers lead walking tours (and one boat trip), including a daily architecture tour that's a fun way to get fresh air during the work day. From $10 (414/277-7795; historicmilwaukee.org).
Why The architecture is interesting, but I'll remember the people and stories behind the buildings: territory disputes, the first white child (named Milwaukee) and the Polish immigrants who populated Brady Street in the 1800s. -- Manya Kaczkowski
Cleveland
Historic Gateway Neighborhood Corp. Actors dressed as historical figures chat with visitors during free tours downtown through a summertime program called Take a Hike! On weekends, dogs are welcome (216/771-1994; historicgateway.org).
Why Lighthouse steps (but no lighthouse) and the buried storefront of a 19th-century theater? Throw in a "chance" encounter with John D. Rockefeller, and I'm suddenly hooked on the city's history. -- Sarah Routh
Indianapolis
Crown Hill Cemetery Guide Tom Davis, who leads walking tours on these 550 acres, calls this Indy's "people museum." From $5 (317/920-2726; crownhillhf.org).
Why You'll hear the stories of locals you've never heard of (and a few you have). Near gangster John Dillinger's grave, you'll see the resting place of a World War I soldier who died in the 1918 influenza epidemic. And he's the one who captured my imagination. -- Danny Lee
Detroit
Wheelhouse Detroit Hip guided bicycle rides offer an intimate view of the Motor City, with an eye toward the city's rich history and postrecession bright spots. From $25; bike rentals available (313/656-2453; wheelhousedetroit.com).
Why On the Farm-to-Fork tour, we saw lush, verdant community vegetable gardens flourishing in the shadow of dilapidated buildings. What a powerful tribute to this city's resiliency. -- Emily Tennyson
Columbus
Columbus Food Adventures Five food-theme van and walking tours include a dessert sampler, a German Village walking tour and a taste of the city's best taco trucks. From $45 (614/440-3177; columbusfoodadventures.com).
Why Ditch your fears of "roach coaches" or language barriers, and learn how to order the amazing red enchiladas from Los Potosinos. -- Cynthia Earhart
Omaha
Durham Museum Chatty, knowledgeable guides hop aboard Omaha's Ollie the Trolley (a local sightseeing staple) for five history tours that start at stunning Union Station (pictured at left). From $15 (402/444-5071; durhammuseum.org).
Why Seeing the stained-glass windows, variegated marble and stately porte cocheres of the city's grand mansions made me daydream about the glamorous events that once led stars and presidents to these doors. -- Tina King
Chicago
Chicago Architecture Foundation Architectural river cruises (several companies offer them) are a must-do, but if you want to delve deeper, the CAF's diverse tour menu includes Skyscraper Express, Macy's on State Street and Downtown Deco. From $5 (312/922-3432; architecture.org).
Why Chicago is an architectural think tank, and every CAF tour reveals something I didn't know about: a Henry Moore sculpture casually tucked in a lobby or Louis Sullivan stained-glass windows casting colored light on the place where Chicago Gospel was born. -- Kit Bernardi
Saint Paul
Summit Avenue Walking Tour This stroll takes visitors past the 19th-century mansions on a truly spectacular residential street. On Saturdays, a musician plays the vintage pipe organ in the James J. Hill mansion, where tours begin. Reservations recommended. $10 (651/297-2555; www.mnhs.org/hillhouse).
Why F. Scott Fitzgerald grew up around here. Seeing how his neighbors used their massive homes to show off their wealth and power, I understood in a new way his fascination with (and resentment of) affluence. -- Gustave Axelson
Cincinnati
Queen City Underground Evening tours of historic Over-the-Rhine take curiosity seekers through the crypt of St. Francis Church and down a makeshift stairwell to a Gothic cellar that once kept barrels of German beer cool. From $20 (859/951-8560; queencityunderground.com).
Why Great storytelling backed up by extensive research (and the fact that you have to sign a safety waiver) makes it feel like you'll literally step into the colorful world of corrupt politicians, boxing stars, Franciscan monks, strong men and the first commissioner of baseball. -- C.M. Tomlin
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