Connecticut's Star‑studded Escape With Colonial Charm And Mine Hill Trails Is Tucked Between New Haven And Poughkeepsie

Litchfield County is one of the largest in Connecticut by area, but the fourth smallest by population, consisting of many quintessential cozy New England towns. One of these, between the larger municipalities of New Haven, Connecticut and Poughkeepsie, New York, is the charming and rural community of Roxbury. Only an hour from Connecticut's Bradley International Airport and 80 miles north of Manhattan, the area is not just another quiet Connecticut town full of colonial charm. It's also been a hotspot for some of the most elite stars in the world, particularly featuring titans of theater. 

Incorporated in 1796, Roxbury was originally named "Shepaug," a Mohegan word meaning "rocky water", referencing the silver and minerals found in its tributaries. It later became a granite mining and iron ore production hub, the remnants of which remain in Mine Hill Preserve, listed on the National Register of Historic Places. Prior to its official incorporation, Roxbury was home to multiple Revolutionary War heroes, including Colonel Ethan Allan, who helped found Vermont. This period of colonial significance is still evident through the town's architecture and memorial sites. In more recent decades, Roxbury became a country getaway and residence for celebrities like Marilyn Monroe and Daniel Day-Lewis.

In 1949, Arthur Miller won the Pulitzer Prize for his epic dramatic play "Death of a Salesman." A year earlier, he had decided to leave New York City for solitude to aid in his writing and settled in Roxbury, where he built a cabin and wrote his magnum opus. Less than a decade later, he married Marilyn Monroe, who joined him in the quiet colonial home on the same property. The land is now the Roxbury Land Trust-managed Arthur Miller & Inga Morath Miller Preserve, in honor of the playwright and his third wife.

Miller and Monroe were pioneers for what would become a growing population of theater, literary, and film figures in Roxbury. Broadway legend Stephen Sondheim maintained a colonial home in the town for over four decades, up until his death in 2021. Fellow Pulitzer-winning author of "Angela's Ashes," Frank McCourt, also lived in the town and is buried down the road from Mine Hill Preserve. Oscar winner Walter Matthau also owned land in Roxbury for 20 years, and his former property is now a Land Trust-owned nature preserve bearing his name. 

More contemporary stars who have called Roxbury home include Meryl Streep, Dustin Hoffman, Daniel Day-Lewis and his wife Rebecca Miller, Denis Leary, and other musicians, artists, and actors. While you might be most likely to spot celebrities in New York, this small town has nearly as much potential in its 26 square miles. Its bigger draw for tourists, though, is the simple serenity from its historic preservation. 

Roxbury's rich mining history is perhaps best experienced in the trails at Mine Hill Preserve, where industrial furnaces were built to process iron ore into steel. The relics at the Preserve itself contain informational signs that offer a sort of self-guided tour of the grounds and former industry. Four miles of hiking trails create a serene escape into the preserve while tucking in views to the former quarries, air shafts, and mine tunnels, as well as granite cliffs and a bat cave. The gray stones themselves are a unique look into the town's history — the granite slabs used here were harvested to build churches and homes throughout the Northeast, as well as Grand Central Station and the Brooklyn Bridge in New York City. 

Just outside the preserve is Mine Hill Distillery, which crafts spirits from locally sourced grain in an 1860 building that once served as a cigar factory. Roxbury Kitchen, one of the few restaurants in the small town, is also nearby and serves pizza, sandwiches, burgers, and more every day except Monday. The trails here marry the quiet, natural beauty of the area with its centuries-old history, a combination that makes it easy to see why so many stars have long called this place home.