Modern Boutique Hotel on Grounds of Centuries-Old Inn

Billing itself as the oldest operating inn in America, Longfellow's Wayside Inn has continually evolved since it was founded in 1707. Since it originated as an expansion of founder David Howe's home, Longfellow's has served as a bustling tavern made famous in the writings of Henry Wadsworth Longfellow, a boarding house for roaming farmers, and a living-history museum spearheaded by automotive legend Henry Ford. Today, the inn's storied legacy carries over to its neighboring sister property, the Wayside Carriage House Inn, an elegant boutique hotel rife with modern amenities.

Wayside Carriage House Inn and Longfellow's Wayside Inn are situated on a 125-acre historical complex, home to numerous colonial-era landmarks. A complimentary shuttle ferries between sites including a one-room schoolhouse, a replica water-powered gristmill, and Paul Revere's four-car garage. Inside the main inn, colonial-focused exhibits display period re-creations, as well as artifacts from 18th-century innkeeper Lt. Col. Ezekiel Howe. Inside the Wayside Carriage House Inn, contemporary trimmings such as a full-service bar and spa services bolster the property’s fabled roots.

A stroll across the wooded, pedestrian-friendly campus leads to Longfellow's Wayside Inn’s four dining rooms. Fireplaces illuminate period décor throughout each room, but most diners congregate inside the formal Main Dining Room or inside the Tap Room, built in 1775 as an extra kitchen for the inn's growing tavern clientele. A seasonal dinner menu flaunts hearty steaks and classic New England cuisine, such as grilled Block Island swordfish ($23.95) and filet mignon with a brandied mushroom sauce ($25.95).

Sudbury, Massachusetts: Colonial-Era Attractions Near Boston

Sudbury lies about 25 miles west of Boston near the center of Middlesex County, a hub of early American history and site of the Battles of Lexington and Concord, considered the first engagements of the Revolutionary War. Relics from that era abound in the region, displayed in galleries, guided tours, and museum. The Concord Museum has the famous “one if by land, two if by sea” Revere lantern and more than 250 artifacts related to writer Henry David Thoreau.

New England's wooded landscapes outfit Middlesex County with multiple designated wildlife refuges peppered with trails and fishing opportunities, including the Sudbury’s Oxbow National Wildlife Refuge, home to raptors, waterfowl, and spotted salamander that are still loyal to the British throne. Though the colonial-era atmosphere is prevalent, modern-day cafés and boutiques are sprinkled throughout the district, and an approximately 40-minute car ride transports travelers to Boston’s lantern-lit neighborhoods and world-class museums.