When it comes to regal charm, it's hard to contend with Southport, Connecticut, a bastion of venerable mansions, pristine marinas and small beaches straddling the Long Island Sound. Granted, you won't find many diversions here, but the ones you will encounter are memorable-including the old-timey Horseshoe Tavern and the Pequot Library, one of the oldest in the country.
A few hours south, divided by the Delaware River, await a pair of beguiling villages overflowing with excellent shopping, dining and nightlife options: New Hope, Pennsylvania and Lambertville, New Jersey. A splendid lodging choice here is the inimitable Lambertville Inn, while Havana's (in New Hope) is one of many reliable restaurants. When it comes to nightlife, John & Peter's Place is a groovy little joint right on New Hope's Main Street with constant live tunes, and the Boathouse in Lambertville is regally relaxing.
On the Gulf of Mexico, Seaside, Florida, is a one-of-a-kind "master planned community" created in 1979, perhaps best known as the shooting location for much of the film, "The Truman Show." This relatively new burg is compact, attractive and well located (across a small highway from the beach), with a town lawn/amphitheater for frequent events, awesome bar with live guitar music on the deck, and some good restaurants too.
While not everyone is thrilled with the "progress" taking place in Oxford, Mississippi in terms of its recent commercial growth, it remains a quintessential southern town with an inviting town square, attractive college campus (the University of Mississippi) and some great mom and pop stores that include one of the best independent bookstores in the country-Square Books.
Nestled on steep bluffs overlooking the Pacific, Mendocino, California is undoubtedly one of the handsomest and most dramatically set communities on the planet. You'll also find plenty to do for a town of only about a thousand residents, from cliffside hikes to boutique shopping to some excellent dining options. The MacCallum House is the place to stay if you have a few bucks to spend, and Dick's on Main Street is a spartanly inviting watering hole with a view of the ocean from a few choice seats.
The Northwest is home to a plethora of enchanting small towns, but none have more personality than tiny Roslyn, in the heart of Washington State. A small museum, a handful of beguiling old cemeteries and a historic "coal miners trail" are among the low-key diversions, and you won't find a better place to unwind in the evening than the iconic Brick Tavern-easily recognized by fans of the old TV show "Northern Exposure."
Marshall might only have a little over 10,000 residents, but you'll find plenty to do in the pleasant and attractive college town in southwestern Minnesota. Much of the activity revolves around Southwest Minnesota University, with some excellent galleries, and the town also has an impressive Arts Center and stage company. The village is at its best in fair weather, as it comprises seven city parks and has two larger parks on its outskirts-including the popular Camden State Park.
When it comes to the small towns of Hawaii, Paia is a favorite of many, with several excellent town beaches nearby and a wonderful general store fixing the perfect sandwiches for a picnic or excursion down Maui's famed Hana Highway. When the nighttime rolls around, two popular neighboring bars on the main street provide evening excitement.