Historic 18th-Century Inn with Candlelit Restaurant

The Old Inn on the Green, with its whitewashed clapboard façade and front porches overlooking rolling meadows, was named one of New England’s Best Historic Inns by Yankee Magazine in 2011. Once a stagecoach relay, the main building has occupied its quiet spot in the Berkshires since 1760. Honey-colored wooden floorboards, antiques, and period pieces nod to the building’s early days. More recent upgrades have included the addition of an intimate bar, which earned a Best in the Berkshires rating from Zagat and was called “one of the finest dining destinations in the area” by Travel + Leisure.

Candles and brick-lined fireplaces are the only sources of light in the dining room, where the chef serves seasonal American fare using ingredients procured from local farmers. This Getaway includes a dinner for two served at the onsite restaurant, with dishes such as slow-braised lamb shank and spring vegetable risotto. In the morning, a complimentary continental breakfast of fresh baked goods, juice, and French press coffee is served. You’ll also enjoy an included lunch at The Southfield Store.

Eleven bedrooms are available between the main building and the separate Thayer House, and all of them have been faithfully restored. The décor varies from room to room—many have fireplaces and some have claw-foot tubs, but all feature authentic antiques that evoke the 1800s. The Thayer House also contains a small library and two shared living rooms.

Berkshires, Massachusetts: Historical Highlands Region with Thriving Arts Scene and Outdoor Recreation

The Berkshires, a mountain range in western Massachusetts, has long served as an inspiration and source of solitude for artists and writers, including Herman Melville and Edith Wharton. Residents in the Berkshires carry on that tradition—it has a thriving arts scene, with a number of repertory theaters and world-class museums.

There’s also plenty to keep outdoor enthusiasts busy. It’s popular to take a leaf-peeping drive through the colorful countryside. Mount Greylock, the highest peak in Massachusetts, is crisscrossed by 70 miles of hiking and mountain-biking trails. The Berkshire Botanical Garden, open May through mid-October, has 15 acres of native plants and topiaries.

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