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The Perfect Weekend Getaway: Traverse City From Chicago

Our new series on weekend road trips aims to inspire you for what's to come as we slowly return to travel.

Covid-19 Disclaimer: Make sure to check the status of the states, regions, and establishments in which you’re planning to visit prior to travel. Many regions continue to see high infection rates and deaths, while many states and counties remain under varying stay-at-home orders. Those traveling from areas with high rates of Covid-19 should consider avoiding travel for now in order to reduce spread. 

With only 16,000 residents and a charming “Main Street” (Front Street), the official cherry capital of the country is—pardon the pun—also a sweet little getaway. Hugging the shores of Grand Traverse Bay, which flows into Lake Michigan, it’s also a wine region receiving accolades from Chicago sommeliers and placing high at national wine competitions. Also, it’s worth noting that ’80s Material Girl Madonna’s family owns and manages a vineyard and winery here (Ciccone Vineyard and Winery) while, in 2014, TLC’s Trading Spaces Carter Oosterhouse (a Traverse City native) founded Bonobo Winery on Old Mission Peninsula with his brother Todd.


The easiest way to reach Traverse City is by car, especially because you’ll need transportation between tasting rooms. From downtown Chicago, the 320-mile trip takes about five hours. A combination of Indian Trails and Greyhound bus lines yields a grueling 10-hour ride, and you’ll still need to rent a car or invest in hefty Uber or Lyft fares upon arrival.


After the five-hour drive from Chicago (plus jumping one hour forward to EST)—and because it’s five o’clock somewhere—you need that first glass of wine, right? But before you do that, check into your accommodations, take a short walk on the beach (West End Beach, with its narrow shoreline and plenty of parking, is close to downtown), and then sit down for an early drink at Left Foot Charley, a wine and hard-cider producer with a chic (think modern-industrial aesthetic) tasting room. Tasting flights ($7) are a quick tour of the portfolio.

For dinner, slip into The Cooks’ House. This downtown restaurant is run by two Michelin-star chefs who came home to Traverse City (from Las Vegas) in 2008. Their farm-to-table and foraged dishes include Michigan Artisan Cheeses plate or a walleye roasted in butter with foie gras cream and sunflower sprouts.


Hit up tasting rooms early so you can space out your sips and also catch morning’s golden light for perfect photos. Just like Napa and Sonoma, most are open from 10 a.m. or 11 a.m. to 4 p.m.-6 p.m. Wineries lie in one of two American Viticultural Areas: Old Mission Peninsula AVA and Leelanau Peninsula AVA.

Kickstart a full day of wine tasting with a hearty breakfast of an egg-biscuit sandwich or French-style omelet at the new Benedict and then buckle up for some wine tasting. The key here to is to work your way south. Start at the far northern

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tip of the Leelanau Peninsula, home to the Grand Traverse Lighthouse and Leelanau State Park (both are along Grand Traverse Bay) for photo-taking ops, then roll into your first tasting room. Green Bird Organic Cellars in Northport is about more than wine. Wines (from Gewürztraminer to Pinot Gris) are organically certified; they make hard ciders too, and you can try both in this 67-acre farm setting, which is also a popular wedding venue. For your designated driver, cherry soda—plus a meat and cheese board—is also served here.

Sample a regional specialty—smoked whitefish pâté, whitefish taco, garlic parmesan whitefish, or items with cherry-chicken flavor, capping off with a slice of cherry pie—at the no-frills The Cove in Leland (don’t leave without checking out the lower-level Rick’s Café). If you feel like you’re in a fishing cabin, that’s the whole idea. Work off all that food with an easy stroll at Sleeping Bear Dunes National Lakeshore, where dunes overlook Lake Michigan and 65 miles of shoreline will make you believe in the healing powers of the Great Lakes.

Curl south to your next winery along Lake Michigan, on M-22. Just two miles in from the Lake Michigan coast, family-owned Good Harbor Vineyards has quietly been making wine from its own vines since 1980. Try six of its wines for $5 seated on the tasting room’s patio. Head to the region’s second AVA (home to fewer wineries) for a quick tour by tasting at Bonobo Winery, founded by TLC’s Carter Oosterhouse. Wines range from the familiar (Chardonnay) to a rosé crafted from eight grape varieties, including lesser-known varietals like Auxerrois and Ariana.

Nap back at the hotel or switch up your clothes for a night “out on the town” Traverse City style (read: comfy but chic). The Filling Station Microbrewery—within a former train depot—is one of the region’s hottest dinner spots (featuring salads and wood-fired pizzas)—and super casual. If you’re tired of wine, you’ll love the craft beers brewed on-site. Treat yourself to a patio seat and lake view and, if available, live music.

INSIDER TIPJarred fruit jams from Art’s Tavern in Glen Harbor make great souvenirs or thank-you gifts for the pet sitter or neighbor who watered your plants.


Need a morning jolt or just want to check out the local café scene? Morsels on East Front Street is a darling brick-exterior café touting an outdoor patio, espresso and coffee drinks crafted from Intelligentsia beans, and its signature “morsels” (doughy cookies with dollops of frosting). Browse three nearby indie bookstores (the wellness-oriented Higher Self Bookstore, Horizon Books and Brilliant Books) for reads to dive into back home.

Black Star Farms’ Suttons Bay tasting room, spanning 160 acres in the Leelanau Peninsula AVA, is the kind of winery you’ll want to spend all day at. After a stroll through the grounds, which includes an inn, hiking trails, cafe and

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equestrian facility, indulge in the Premium Wine & Cheese Tasting at noon or 2 p.m. (reservations required by midnight the day prior). Want to do a comparison tasting? Nearby Mawby Vineyards and Winery is another sparkling-wine producer and open to visitors, sourcing grapes from its own vineyards as well as from across the U.S. for greater diversity.

Swing by Cherry Republic in downtown Traverse City and scoop up some dark-chocolate-covered cherries and slices of cherry pie for the ride back to Chicago. Even the wines this brand makes are crafted with cherry (try them in the store). But before heading home, roll into The Little Fleet, a community of rotating food trucks parked on East Front Street year-round for gourmet grub. Your early dinner might be Happy’s Taco Shop’s tacos or ‘cue from Cordwood, paired with a farm-to-table cocktail or spiked slushie from The Big Squeeze, a mobile bar.


There are more boutique inns, guest houses, and Airbnbs than chains in Traverse City. Sleep near the vines at Brys Estate Vineyard & Winery’s former barn turned luxe mod farmhouse on the winery’s 111-acre estate—reservations include a charcuterie board, bottle of wine, wine tasting and glass of wine for each guest—or “in town” at Bayshore Resort, which hugs the beach and is a short walk to East Front Street.


Like most Upper Midwest destinations, summer is when crowds converge for the year’s warmest temps, cherry season (early July through early August), and true beach weather. But shoulder seasons—spring and fall—are when you can chat with winemakers and, come fall, experience harvest. Avoid the National Cherry Festival in early July when hotel rooms are booked.