Explore our Two-Day Tour of the Litchfield Hills

Explore our Two-Day Tour of the Litchfield Hills

From art and history to vineyards, amusement parks and more, there’s so much to see and do in Litchfield Hills. To help you plan your trip, we’ve provided this handy guide showing the best places to explore throughout the area.

Day 1

Stop #1: Take a trip back in time at the  Keeler Tavern in Ridgefield. Dating to 1713, this house was a tavern, stagecoach stop, post office, hotel and home of architect Cass Gilbert

Stop #2: Tour the Danbury Historical Society, Marian Anderson Studio & the John Dodd Hat Shop, which details the process of hat production that made Danbury the “hat capital”.

Lunch: Enjoy all your favorite foods when you stop for lunch at Elmer's Diner.

Stop #3: Visit the New Milford Historical Society Museum and explore the town’s rich history through a main gallery connected to the Knapp House (c.1815), the first bank in town c.1822, and a 1796 Mercantile Store.

Stop #4: Tour The Glebe House & the Gertrude Jeckll Garden in Woodbury. This 1750s minister’s house, decorated with period furnishings, where the first Bishop of the Episcopal Church was elected in 1783. Explore the only garden in the U.S. designed by Gertrude Jeckll, the most famous 20th-century British gardener.

Stop #5: Watch as traditional and contemporary designs are made at Woodbury Pewter in Woodbury on the premises using age-old techniques. View a demonstration in casting of custom pewter and see how a teapot is made from start to fi nish. 

After dinner, take in a performance at one ot the local theaters:


Day 2

Stop #1: Explore American art and cultural history at the Mattatuck Museum in Waterbury and discover more than 25 changing exhibitions each year.

Stop #2: Learn about the history of the American made clocks and watches at the American Clock and Watch Museum in Bristol. While exploring the galleries of this museum that house the largest display of American production clocks in the world.

Stop #3: Take a guided tour of The New England Carousel Museum located in Bristol. View the museum’s galleries, enjoy a ride on a working carousel and visit the restoration shop.


Stop #4: Enjoy a scenic vintage train ride on the Naugatuck Railroad in Thomaston that departs from a historic 1881 train station. rmne.org

Stop #5: Investigate the evolution of a small New England Village through exhibits at the Litchfield History Museum and Tapping Reeve House & Law School in seven galleries and visit America’s first law school. 

Stop #6: Tour the gracious 1754 Bellamy–Ferriday House in Bethlehem. Bethlehem’s First Minister transformed into a 20th-century country estate of Caroline Ferriday.