First, a few logistics: A few of the finest beaches like Nauset Light have a limited amount of parking, a reason to sport a bike around town (rentals are easy to organize). Also, weekly house rentals start and end on Saturday, so if you can avoid crossing the bridges on that day, it will be a lot easier to get in and out. Without a wetsuit, summer is the only time to brave the ocean. Those cool waters and the pounding surf are the reasons why younger families retreat to the calmer bay side or to one of the ponds. Mid-June to mid-August is also the time of year to catch a Cape Cod Baseball League game. It’s the premier amateur league in the States, and one in seven current MLB players have played here.
Many locals can’t wait until September, when the crowds leave. If you’re one of the fortunate people who can stick around, you’ll have sublime beach weather and the opportunity to reserve a table at your favorite restaurant with no problems. Many hotels and restaurants stay open until at least mid-October, so you don’t have to worry about the place shutting down.
Only writers who need to finish a book on deadline and artists who relish the quiet can handle the Cape in winter. Many motels and restaurants outside of the main towns of Hyannis, Orleans, and Falmouth are closed. Seek higher ground or a city with an energetic core.