Orchards, Wineries, and Quiet Shorelines in Michigan’s Leelanau County
Roughly 330 miles from Chicago lies one of the Midwest’s great natural treasures: a landscape shaped by dunes , orchards, vineyards, inland lakes, and miles of wooded shoreline. Many Chicagoans know southwest Michigan well—a wedding at Journeyman, a retreat in New Buffalo, a farm dinner at Granor—but farther north, Leelanau County offers a different rhythm entirely.
Framed by the waters of Lake Michigan, this peninsula is a place of quiet beaches, working farms, small towns, and surprisingly good wine, where agriculture and natural beauty remain deeply intertwined. If the Old Mission Peninsula is Napa, Leelanau is Sonoma—or for East Coast travelers, think a quieter Shelter Island to Montauk’s bustle.
Bordered on three sides by Lake Michigan, Leelanau County encompasses more than 100 miles of shoreline, 33 inland lakes, and five islands: North Manitou, South Manitou, North Fox, South Fox, and Gull Island. The region sits on the ancestral lands of the Anishinaabeg and the Three Fires Confederacy of the Ojibwe, Ottawa, and Potawatomi peoples.
The region shares a latitude with the renowned wine regions of France. That geographic similarity—when combined with the thermal impacts of Lake Michigan and the enthusiastic stewardship of a new generation of wine makers—makes for a Midwestern force to be reckoned with.
Getting There
For travelers who appreciate a more hands off mode of transportation, flying into Traverse City offers quick access from across the Midwest and beyond. But if time allows, the drive from Chicago is part of the experience. The roughly 5.5-hour journey hugs the lakeshore and passes through beach towns, farmland, and small communities worth lingering in. Break up the trip with breakfast or lunch at Pennyroyal Café and leave room for a few detours along the way—you’ll be glad to have a car once you arrive.
Where to Eat
Part bakery, farm market, and gathering place, 9 Bean Rows is beloved for wood-fired breads, seasonal pastries, and produce-driven lunches rooted in local agriculture.
A quintessential Fishtown stop known for its riverside setting, fresh whitefish, and baskets of fish and chips enjoyed steps from the harbor.
Part brewery, farm, restaurant, and bakery, Farm Club celebrates hyperlocal ingredients with wood-fired cooking, house-fermented beverages, and expansive gardens visitors can explore.
This intimate Suttons Bay restaurant pairs thoughtful seasonal cooking with a warm atmosphere, showcasing the bounty of northern Michigan through refined but approachable food.
Think of it as a Disneyland for cherry enthusiasts, with cherry-forward dishes, preserves, wines, and enough tastings to fully embrace Michigan’s signature fruit.
An artisan chocolate shop focused on ethically sourced cacao, offering beautifully crafted confections and drinking chocolates in the heart of Empire.
Where to Stay
Ideal for families or longer stays, this lakeside resort combines beach access, trails, golf, and village-style accommodations near Sleeping Bear Dunes.
A thoughtfully restored historic property offering a more intimate stay, blending luxury touches with easy access to Glen Arbor and the lakeshore.
Vineyards to Explore
A small, family-run vineyard producing low-intervention wines with sweeping views and a focus on expressing Leelanau’s cool-climate terroir.
One of the region’s long standing wineries, known for approachable pours, sparkling wines, and a relaxed tasting experience near the lakeshore.
A newer addition to the Leelanau wine scene, offering panoramic water views and estate wines in an architecturally striking tasting room.
Set within a historic estate, Shady Lane pairs elegant wines with one of the peninsula’s most beautiful vineyard settings.
A modern winery and tasting room emphasizing sustainability, expressive wines, and a welcoming atmosphere for lingering over a flight.
Perched high above Lake Michigan, Rove is known as much for its breathtaking views as its crisp cool-climate wines.
Places to Wander
This preserved fishing village in Leland offers weathered shanties, smokehouses, docks, and shops that capture northern Michigan’s maritime history.
Sleeping Bear Dunes National Lakeshore
Towering dunes, forested trails, and sweeping lake views make this one of the Midwest’s most spectacular natural landscapes.
A walkable lakeside town filled with boutiques, galleries, cafés, and easy access to beaches and wineries.
Part farm, market, and community hub, this stop offers produce, flowers, local goods, and postcard-worthy views over the countryside.
