Hillside, once home to famed novelist Winston Churchill, is located in Plainfield, New Hampshire and is part of the artists colony in the region that includes Cornish, New Hampshire. It is in the Upper Valley and is near the towns of Hanover, New Hampshire and Woodstock, Vermont. It is within easy access along NH Route 12A to shopping, ski resorts, health care services, schools, exercise facilities and golf courses. An overview of what's nearby is below.

Plainfield & Cornish, New Hampshire

Back in the late 1700's, Cornish, New Hampshire was known simply as  "Mast Camp" as it was a shipping point along the Connecticut River for the strong, tall and straight white pine trees used as Navy ship masts. However, Cornish -- named after a Royal Navy captain -- really came into popularity as the 19th century "discovery" of sculptor Augustus St. Gaudens. Soon, through St. Gaudens' connections to the Art Students League of New York and a convenient passenger train to Windsor, Cornish & Plainfield became a destination for New York and Boston artists, writers, politicians and bon-vivantes attracted to the community's peaceful farms and riverbanks along the Connecticut River. 

Atrium Fountain at St. Gaudens National Historic Site

Atrium Fountain at St. Gaudens National Historic Site

Hanover, New Hampshire

Hanover is home to Dartmouth-Hitchcock Medical Center, boutique shopping outlets, fabulous food, and more. One of its main attractions is Dartmouth College (one of the Ivy Leagues and the ninth oldest college in the nation), and in part due to its youthful atmosphere, the town enjoys a lively, 'New England cosmopolitan' business district. Hanover offers an incredible mix of activities from access to the White and Green Mountains to its arts and culture community not to mention the obvious intellectual benefits found in a college town. The Dirt Cowboy (pictured below) at the top of South Main Street is one of the best places to meet someone on any morning.

A view of Main Street in Hanover

A view of Main Street in Hanover


Woodstock, Vermont is the quintessential New England historic town. It sits in a valley surrounded by low-lying hills that nestle rather than overwhelm, and is a community snuggled around the Ottauquechee River. Woodstock is home to many excellent shops and restaurants, the Woodstock Inn & Resort, a great middle and high school, and it never fails to serve as an incredible place to go for a walk or meet someone for coffee. 

Those who choose to reside near Woodstock continue to be some of the most educated in the world, some of the most accomplished “captains of industry” in the country.  You’ll find filmmakers, war correspondents, writers, artists, military experts, doctors, high-tech entrepreneurs, rock stars, equestrians and happy soccer moms and dads all grabbing a coffee in town. Woodstock also attracts its fair share of Dutch, English and French, many of whom are reminded of home by the gentle hills, winding dirt roads, cows, sheep and horses in pastures next to beautiful weathered barns. Even if it’s not the old country, it has the feel of a place with deep roots.



Killington Mountain is one of the best places to go skiing in Vermont. With a summit elevation of 4,241 ft, 22 lifts, 155 trails and 1,509 skiable acres you will not be disappointed.