Island in Flux | September

Jean Guichard/Corbis

Block Island offers up two quintessentially New England lighthouses.

Truthfully I’m somewhat loathe to sing the praises of Block Island in September, and it’s not because I don’t love it there. I do. In fact, to my mind, there are few places as lovely, particularly on a crisp fall day. And that’s the problem: As a lifelong devotee, I feel deeply protective of the island. I’m wary of encouraging too many visitors to set their course for Block Island next fall. However, in the spirit of sharing, I’ll let you in on why so many others and I think it’s such a spectacular destination. Just please, promise you’ll be discreet.

Block Island is a small spot of land that sits about ten miles south of the Rhode Island mainland. It’s often described as the most laid-back of the “major” New England island destinations, and while that might be the case, come midsummer it moves at a frenetic pace. The beaches are full of families, the marinas overflow with boats, and the roads are abuzz with mopeds. However, once Labor Day rolls around, the island empties out.

Don’t get me wrong, it’s hardly a desolate place. There are still plenty of people around, and there’s no shortage of things to do. I’m partial to spending lazy afternoons strolling through the island’s sole town. The streets are lined with Victorian Gothic buildings that house restaurants, boutiques, and galleries. Once you’ve had your fill of browsing, head over to New Harbor, which offers up three full-service marinas. While some of the docks are removed after Labor Day, it’s still a beautiful spot to see. As dusk rolls in, grab your sweater and head up to The Oar, a casual restaurant that fronts the harbor. It has a wide deck with a long bar that’s the perfect spot to sit and watch the sun dip into the water. Just one thing: If you do go, make sure to tip your server well (I used to be one).

The beaches are quiet, come September.

If you’re an outdoorsy type, Block Island has got nature in spades. Rent a bike, and weave your way over the hilly roads that lead to the Mohegan Bluffs. You’ll be rewarded with breathtaking vistas of the quintessential New England coastline. A few hundred feet away, you’ll find the Southeast Lighthouse, which was built in 1875. It had to be moved back from the cliff’s edge in the mid-1990’s due to the threat of erosion. As you make your way back north, stop in Rodman’s Hollow, an aptly named depression that’s lined with various walking trails. It’s a particularly pleasant outing in September when the shrubs and trees come alive with migratory birds. When you’re ready to hit the water, there’s great light-tackle and saltwater fly-fishing for bluefish, bass, false albacore, and bonitos.

No matter what your cup of tea, the nicest thing about visiting Block Island in September is that the island is in a delicious state of transition. It’s not quite summer, nor is it fall. Things are slow and quiet. It’s worth checking out. Just remember—shhh.

Destinations To Die For

January: Plymouth Harbor, Dominica
February: The Spanish Virgin Islands
March: Mazatlan, Mexico
April: Man-O-War Cay, Bahamas
May: Southport, North Carolina
June: Greenport, New York
July: New York, New York
August: Penobscot Bay, Maine
September: Block Island, Rhode Island
October: Panama City, Florida
November: Key West, Florida
December: Staniel Cay, Bahamas

This article originally appeared in the December 2007 issue of Power & Motoryacht magazine.