New England–Style Inn with Modern Luxuries

The gilded steeple atop The Westport Inn fits in perfectly along this stretch of coastal New England, where main streets are dotted with churches and clapboard general stores. A thriving arts community livens up Westport's staid colonial roots, and the inn's recent renovations seem to embody the town's personality—abstract paintings hang from the walls amid restorations of original fixtures, including the stone fireplace in the lobby.

At The Westport Inn's Eramosa Restaurant, farm-to-table fare graces uncovered wooden tables for breakfast and dinner. The hearty morning menu lists items such as Farmer's Garden omelets, egg sandwiches topped with thick-cut bacon roasted in pure maple syrup, and organic tea. American comfort fare dominates the evening lineup, with a focus on naturally raised ingredients sourced from local farms for healthy, hormone-free meals.

Rustic wicker chairs and vases filled with twigs lend an earthy quality to the classic rooms. In the bathroom, guests can surround themselves in relaxing, natural scents without bathing in a pile of burning leaves thanks to a stock of all-natural products by UK-based Aromatherapy Associates. Feather bedding adds to the room's old-fashioned feel, though the room also dons modern luxuries such as LCD TVs and iPod docks.

Westport, Connecticut: Coastal Town Steeped in Art and Culture

Once a farm town on the decline, Westport got a fresh start at the turn of the 20th century as it welcomed an influx of writers and artists retreating from the hustle and bustle of New York City. Creative types continue to flood the area, and a metropolitan feel mingles with the quaint, rural atmosphere. The town's seasonal playhouses, performing-arts pavilions, and fine-arts festivals start to draw open their curtains in late spring, and families can take advantage of the winter season by twirling in circles at ice-skating rinks or by group-hugging a snowman before it dies.