A Friends’ 4-Day Fall Adventure

For some ideas on what to do during the autumn season, consider this suggested 4-day itinerary. When planning for larger groups, be sure to book early, make restaurant reservations ahead of time, and consider staying together in a vacation rental.

Day 1

Start your day at Uncommon Coffee Roasters, where you can grab a great cup of joe and some breakfast treats. Then experience the windswept waters of Lake Michigan on a sailboat manned by a local captain who can give you insider tips on area hotspots and a few pointers on how to rig a sail. Discover options for sailing excursions here. Or climb aboard a fishing charter with Best Chance Too Charters, InShore Adventures, or MIRYHA Charters and see who can catch the biggest salmon or trout. Have a late lunch at Wally’s Bar & Grill to try out some of their famous fried perch, fresh from the Great Lakes. Then burn off some calories by climbing Mt. Baldhead and treating yourself to some incredible autumn views. Then make your way over to The Southerner for some outstanding drinks and dinner with a waterfront view. For some outrageous evening fun, head to The Dunes Resort for Drag Queen Bingo, karaoke, or a cabaret show.

Day 2

Grab breakfast at Ida Red’s Cottage, a Saugatuck local favorite and cash-only establishment you won’t want to miss. Then take a cruise aboard the Star of Saugatuck paddlewheel boat during weekends through October for stunning views of the beautiful fall landscape. Afterward, take to the trails and explore the gently rolling dunes and shoreline of the Saugatuck Harbor Natural Area or the sandy forest paths of Saugatuck Dunes State Park, where you can take in the fall colors at their peak. For more water views to enjoy, plan on a stop at The BARge for lunch or happy hour. Rent bikes from Blue Star Barns and explore the many downtown shops and boutiques. Finish out your evening at Coral Gables either at their piano bar or listening to some stand-up comedy.

Day 3

Enjoy some delicious coffee and breakfast from Respite Cappuccino Court in Douglas before making your way to Fennville. There, plan on going apple picking at Crane Orchards, where you can also indulge in some fresh cider and donuts. Then challenge yourselves through their 20-acre, intricately designed corn maze, available September through October. Once you’ve made it out, you’ll want to have lunch at Crane’s Pie Pantry Restaurant & Winery, where you can sample their delicious fruit pies by ordering their famous Pie Flight. After enjoying some downtime together, head to Oval Beach to catch a sunset over Lake Michigan. Plan to have dinner back in Fennville at Salt of the Earth for some delicious farm-to-table fare, and where chances are good, you’ll be able to catch some live music.

Day 4

After sharing brunch at Pumpernickels, explore our region’s finest microbrews with a craft beer tour at Saugatuck Brewing Company, Waypost Brewing Co., and the Mitten Brewing Company. Bring your designated driver or charter a private tour through Coastal Tours, Singapore Shuttles, or Untapped Sights & Tours for worry-free transportation. When it’s time for dinner, engage in some friendly competition at Alley’s All American Diner, where you and your crew can indulge in some great pizza and then bowl against each other for bragging rights.

Have a bit more time? Stay for a week and add to your adventure with the following activities.

Go for a gallery stroll.
Explore our many galleries and bring home your own covet-worthy conversation piece. Check out the Saugatuck Center for the Arts and Ox-Bow House for exhibits and open markets.

Play a round of golf.
Hit the links at The Ravines Golf Club or Clearbrook Golf Club. Each provides idyllic views, challenging golf, and extraordinary clubhouse experiences.

Take a private vineyard tour.
Explore the art of winemaking with a behind-the-scenes tour. Modales, Fenn Valley Vineyards, and Michigan Wine Co. let you learn from the experts in a group setting or through a private tour.