Nestled on the Leelanau Peninsula, Leland, Michigan, offers breathtaking scenery, small-town charm, and a close-knit lakeside community. While many are content to bask in its beauty year-round, Leland also provides the perfect launching pad for weekend adventures across northern Michigan and beyond. Whether you're craving a relaxing escape or a culture-filled city break, you'll find enticing options just a short drive away.
If you’re lucky enough to call Leland home—or are thinking of making the move—this list of weekend trip ideas is your passport to unforgettable experiences across the region.
1. Traverse City, MI – A Local Gem with Global Flavor
Distance: 30 miles | Drive Time: 45 minutes
Traverse City is a go-to weekend destination for many Leelanau residents—and for good reason. Known as the Cherry Capital of the World, this bustling small city offers a vibrant mix of culinary delights, wine tasting, lakefront activities, and year-round events.
Spend your day strolling downtown boutiques, enjoying farm-to-table fare at spots like The Cook’s House or Trattoria Stella, and sampling local vintages at Brys Estate or Bonobo Winery. In the summer, the beaches of West Bay are ideal for sunbathing and paddleboarding, while winter brings cozy charm to Front Street and nearby ski trails.
Don’t Miss: Traverse City Film Festival (July), National Cherry Festival (early July), and the extensive TART trail system for biking and walking.
2. Petoskey, MI – Victorian Charm on the Bay
Distance: 85 miles | Drive Time: 2 hours
Located along the Little Traverse Bay, Petoskey is a picturesque town with historic architecture, boutique shops, and plenty of outdoor adventure. Wander through the Gaslight District or head to Petoskey State Park for a scenic hike and a chance to hunt for the region’s famous Petoskey stones.
It’s also a great place to explore Michigan’s literary legacy—Ernest Hemingway spent many of his formative years here, and his spirit still lingers in the historic downtown.
Weekend Tip: Stay in a charming bed-and-breakfast or a historic inn for a romantic, nostalgic retreat.
3. Mackinac Island – A Step Back in Time
Distance: 120 miles (to ferry port) | Drive Time: 2.5 hours + ferry
If you’re looking for an escape that feels like stepping into a storybook, Mackinac Island delivers. With no cars allowed, the island moves at a slower, more peaceful pace. Horse-drawn carriages, Victorian-era buildings, and world-famous fudge define this Lake Huron treasure.
Bike around the island’s 8-mile perimeter, visit historic Fort Mackinac, or enjoy high tea at the iconic Grand Hotel. Whether you go for history, nature, or pure relaxation, a weekend here feels timeless.
Travel Tip: Book ferry tickets in advance during the summer peak season.
4. Charlevoix, MI – Waterways and Whimsy
Distance: 70 miles | Drive Time: 1.5 hours
Charlevoix’s vibrant downtown sits between Lake Michigan and Lake Charlevoix, offering one of the most scenic harbor towns in the state. Browse art galleries, grab ice cream at Kilwins, and admire the storybook Mushroom Houses designed by Earl Young.
Boating, kayaking, and sailing enthusiasts will find plenty to do here, and the local dining scene continues to grow, with gems like The Boathouse and That French Place.
Bonus: The annual Venetian Festival (late July) offers fireworks, parades, and live music along the waterfront.
5. Sleeping Bear Dunes National Lakeshore – Nature’s Playground
Distance: 25 miles | Drive Time: 40 minutes
If your ideal weekend includes hiking, beach days, or stargazing, Sleeping Bear Dunes is practically in your backyard. This national lakeshore is one of the crown jewels of northern Michigan, with towering dunes, scenic overlooks, and miles of pristine beaches along Lake Michigan.
Climb the Dune Climb, drive the Pierce Stocking Scenic Drive, or explore Glen Arbor’s laid-back cafes and shops. Camping is available for the rustic-minded, or opt for a cozy rental cabin for the full Up North experience.
Pro Tip: Arrive early to beat the crowds, especially on warm weekends.
6. Harbor Springs, MI – Quaint and Quiet
Distance: 90 miles | Drive Time: 2 hours
Tucked against the base of a forested bluff, Harbor Springs is a favorite getaway for those seeking calm waters, charming streets, and fantastic golf. The town is known for its sailing culture, and its marina is one of the prettiest on Lake Michigan.
Stroll the waterfront, check out local artist galleries, or book a tee time at True North Golf Club. In the colder months, nearby ski resorts like Nub’s Nob and Boyne Highlands draw winter sports lovers.
Why Go: A quieter alternative to busier towns with a timeless, upscale feel.
7. Grand Rapids, MI – Arts, Brews, and City Vibes
Distance: 140 miles | Drive Time: 2.5–3 hours
For a more urban experience, Grand Rapids offers a thriving arts scene, cutting-edge cuisine, and a nationally recognized craft beer culture. Visit the Frederik Meijer Gardens & Sculpture Park, explore the Grand Rapids Art Museum, or take a self-guided brewery tour through Beer City USA.
It’s also a fantastic city for live music, with venues like The Intersection and GLC Live hosting big-name acts and local talent alike.
Stay Tip: The Amway Grand Plaza Hotel offers a historic downtown experience with luxury amenities.
Why Leland Makes the Perfect Home Base
One of the joys of living in Leland is that you don’t have to choose between secluded lakeside living and access to vibrant regional destinations. Whether you're an adventurer, a foodie, or simply enjoy discovering new places, the Leelanau Peninsula is uniquely positioned for weekend getaways that feel far-flung without requiring long travel days.
Living in Leland offers the kind of lifestyle many dream of—quiet, scenic, and deeply connected to nature, with spontaneous access to some of Michigan’s most beloved towns and landscapes.
Ready to Make Leland Your Home?
If the thought of waking up near Lake Michigan and planning weekend escapes to charming towns and natural wonders excites you, it’s time to explore your real estate options. The team at
Leelanau Living Realty Group is your trusted local expert, helping buyers find their dream homes in Leland, Traverse City, and throughout the peninsula.
Whether you’re searching for a year-round residence or a vacation retreat, their in-depth knowledge of the area and passion for Northern Michigan living sets them apart.
