Three generations of women spread out in the grassy rows at Crane Orchards in Fennville, Michigan. Near the Golden Delicious, my daughter Sarah recounts last weekend’s tailgating party. Amid the Empires, my sister Traci talks about settling into her new apartment. In the Cortlands, I tell my mom about an upcoming marathon. Suddenly, my sister Julie bursts into laughter. A half-eaten apple still hangs on a tree. We laugh hysterically for no real reason—and that just makes us laugh more.
If you’d asked, I’d have said it was impossible to get us all together, but all it took was suggesting a place and a time. Apple picking. Crane’s. Sunday. And everyone’s commitments magically disappeared. First my sisters signed on. Then my mom and daughter. But I drew the line when my niece asked if she could bring her boyfriend. No boys allowed.
Baskets full (but conversation still flowing), we head back to my place. I pull out my stained copy of Eet Smakelijk, the Dutch cookbook that’s in just about every kitchen in Holland, Michigan. (The title translates to bon appetit.) It falls open naturally to Dutch Apple Pie, a family tradition, the pie our grandma always made. We pour wine and start slicing, already wondering where to go next.
If you decide to take a weekend trip to the area around Crane Orchards, make Saugatuck, Michigan, an artsy beach town 9 miles northwest of Fennville, your home base. (269) 857-1701; saugatuck.com 
What to do
Crane Orchards Apple picking usually runs through October, but call first to see what varieties are available. (269) 561-8651; craneorchards.com 
Where to eat
Crane’s Pie Pantry The orchard’s hugely popular restaurant serves (not surprisingly) a not-to-be-missed apple pie. Put your name on the hostess list before you pick apples. Or, on the weekends, you can order pie at the window to eat alfresco at the picnic tables. See reviews and ratings.  (269) 561-2297; cranespiepantry.com 
Marro’s Restaurant Even budget diners can enjoy this white-tablecloth Italian restaurant. Gourmet pizzas start at just $7.25. (269) 857-4248; marrosrestaurant.com 
Where to stay
Serendipity Bed-and-Breakfast and Suites The fireplaces in this B&B’s five suites and cottages beg for late-night chats. Breakfast arrives daily in a basket at the door. From $155. (269) 857-3400; serendipitybandbsaugatuck.com 
(A version of this story appeared in Midwest Living® September/October 2010. Prices, dates, and other details are subject to change, so please check specifics before making travel plans.)