Connecticut Map

Connecticut State Route 169

32 miles (51 km)
One hour without stopping or one full day to visit places along the way.
The only fees are at select attractions.


Consider everything you know about New England -- spectacular autumn color, historic buildings, charming cities -- and you will have an idea of what you will find on Connecticut Route 169. Much has changed over the years on this Byway, but the history and traditions of the area are still very much a part of the lives of the people who belong to the communities.

Take the opportunity to experience some of the sights along this historical stretch of road. Visit the beautiful churches in Pomfret that date back to the 1800s. Or find out what life was like for a prosperous family in the mid-19th Century at the Bowen House Museum in Woodstock. Or simply explore some of the towns at your leisure, admiring the distinctive architecture and well-kept parks.

As you travel the Byway, you will visit many wonderful communities. Don't miss the chance to tour each one! The route crosses through Lisbon, where the feeling of an early American community is still evident. Explore Canterbury, where Connecticut's interpretation of Georgian architecture is prominent. Then you will find yourself in Pomfret, once known as "the other Newport" for its strong influx of wealthy summer vacationers. Finally, you will pass through Woodstock, with its many architectural surprises clustered around a town common. Traveling this Byway, you will sense an area that is moving ahead in the times while still maintaining a sense of pride in its history.

Points of Interest

Points of Interest Along The Way

Air Line Rail Trail (CT)

The Air Line Rail Trail stretches across more than 50 miles of land from near the Connecticut River to the Massachusetts border. Panoramic views of the tumbling hills and valleys emphasize the beauty of the trail and surrounding area.

Brooklyn (CT)

With several National Register Historic sites, Brooklyn is a priority stop for the history hunter. Visitors will find places like the Old Brooklyn Burying Ground, a classic 18thcentury cemetery with all the charm and mystery. Fine examples of18th century gravestones can be found here, most notably those of the family of Israel Putnam.

The fairgrounds of the Brooklyn Fair are located here.The Brooklyn Fair has been operating since 1852 -- the oldest continuously operated agricultural fair in the United States. It is held annually the weekend preceding Labor Day. The fair offers agricultural exhibits, competitions, historical displays, and more.Friendship Valley Inn is also on the National Register of Historic Places. As a stop on the underground railroad, this house has been a harbor for travelers for nearly two centuries. It was the home of George Benson, a quaker. He sheltered and supported Prudence Crandall during her trial. Crandall gave the house its name to show appreciation for the kindness shown to her.

In addition to these sites is the Brooklyn Green that holds a cluster of buildings -- many of which have existed since the 1700s. A visit to Brooklyn is a visit to history.


Midway on the Byway.

Brooklyn Green (CT)

The Brooklyn Green holds its own little cluster of history, and visitors are welcome to explore as they travel through Brooklyn on SR-169. Few places in historic New England have 5 churches on the same green combined with several other historic sites. Places on the Brooklyn Green include:


In the town of Brooklyn on the byway.

Canterbury (CT)

New England Charm

Settled in 1697, Canterbury was named for Canterbury in Kent,England, but it has its own New England charm. Among its many historical qualities, it also features an agricultural past in a place called The Grange. Members of the agricultural organization began meeting at the Grange in 1887. The current hall was built in1915.

The Town Green

In the tradition of the New England settlement, Canterbury also features the Town Green where visitors will find the Congregational Church, built in 1964 to resemble the building that resided therefrom 1804. The one-room schoolhouse that was used until the 1940'sis also located on the Town Green.

Prudence Crandall Museum

Perhaps the most notable historical site in town is the Prudence Crandall Museum. The building was originally the first academy for young black women in New England in the 1830s. Although she was persecuted in her own time, she is now considered a heroine.Visitors can explore the Federal/Georgian-style house and all the exhibits that are included there.

Visitors in Canterbury will enjoy a stop that will allow a glimpse of Connecticut's early American past.


Toward the south end of the byway.

Lisbon (CT)

Historical Lisbon

Originally part of Norwich, Lisbon was named as a district in1718, although at the time it was known as Newent. The center oftown is still known as Newent, but Lisbon became the town name in1786 when resident merchants, Hezekiah and Jabez Perkins, began totrade with Lisbon, Portugal.

Bishop House Museum
Today, Lisbon is home to several historical buildings. Among these is the Bishop House Museum, which was built in 1810. It features a combination of colonial and federal architectural styles with an indoor well and attic smoke chamber.

Newent Congregational Church
Built in 1858, this Greek Revival building was the third for the congregation. The steeple was built in the early 1900s, but it houses a bell that was cast in 1820.


At the south end of the byway on SR 169

Natchaug State Forest (CT)

"Natchaug" is a Native American word meaning "land between the rivers." This state forest occupies a portion of the former hunting grounds of the Wabbaquasset Indians between the Bigelow and Still Rivers. Today, visitors can enjoy hiking, fishing, kayaking,canoeing, and horseback riding in the area. The forest offers one of the state's two equestrian camps, the Silvermine Horse Camp, and many visitors also enjoy birding.


Leaving Pomfret, take SR-169 south. At the junction with US-44, turn right and head west for until you reach the park.

Orchards (CT)

Apple orchards found along the byway offer a refreshing and delightful stop for a hungry traveler. Try stopping at the following orchards:


There are two main apple orchards that are found on SR-169.

Pachaug State Forest (CT)

Located along the eastern border of Connecticut, the Pachaug State Forest offers outdoor adventures such as camping, hiking,snowmobiling, fishing, swimming, and boating.
Botanists and wildlife enthusiasts may have the opportunity to witness unusual or exciting species.


Leaving Lisbon (the southernmost point on the Byway), go south on SR-169 until you reach the junction with I-395. Turn left and take I-395 east until you reach the park on your right.

Pomfret (CT)

The Mashamoquet Purchase
Pomfret was settled during the earliest times of colonization inthe New England area. As a result, the Pomfret that visitors find today features several historic buildings and churches. The town began as the "Mashamoquet Purchase" in 1686 and was incorporated in1713.

Walking Trails
In addition to the historical sites of Pomfret, visitors will find walking trails to satisfy an appetite for the outdoors. The Connecticut Audobon-Pomfret Farms offer five miles of trails through a 280-acre preserve. The Air Line Trail includes 12 miles of walking trails along the old railroad bed.

Historic Places
Among the many sites of Pomfret, some of the following are listed with a bit of history.

Pomfret offers many points of interest for travelers who want to see the evolution of colonial Connecticut.


Toward the northern end of the byway between Brooklyn and South Woodstock.

Prudence Crandall Museum (CT)

Crandall, Prudence (1803-90), American teacher and reformer, born in Hopkinton, Rhode Island, of Quaker parentage. In 1831 she established a private school for girls in Canterbury, Connecticut offering a cultured education, including classes in moral philosophy, music, drawing and French, taught by a gentleman. Her efforts to groom women into young scholars were praised in the well-to-do village of Canterbury until Crandall entertained radical notions of admitting black students in her school. Then trouble started. In 1833, she admitted a black girl into the school, Sarah Harris, 19, who carried hopes that she would one day become a teacher of her own people.

Her enrollment of young ladies and little misses of color aroused the violent opposition of her neighbors. She lost her white patrons, and in 1833 she decided to open a school exclusively for young ladies and little misses of color. She received 15 or 20 black pupils. Locals welcomed her pupils by smearing cow manure on the steps, throwing eggs and stringing up a dead cat on the front gate. Her neighbors, by boycott, insult, abuse, and enforcement of an obsolete vagrancy law, tried to close the school. Public meetings were called, petitions were circulated, and a few months later State Sen. Andrew Judson pushed through the legislature a Black Law that barred out-of-state black students, forbade anyone to set up or establish any school for education of nonresident blacks, or to instruct or teach in any such school without the consent of local authorities. For resisting this law Prudence was arrested, imprisoned, and, in October 1833, convicted of educating blacks whom the judge said were not subject to constitutional guarantees of equal rights.

In July 1834, the court of errors reversed the decision on a technicality. Soon afterward her house was attacked and partially destroyed, and she abandoned her project. The affair intensified the conflict between the abolitionist and anti-abolitionist elements, forcing Crandall, after marrying, to spend the remainder of her life in Illinois and Kansas.

The building now houses a museum for visitors to tour.


Located in the town of Canterbury at the intersection of SR169 and SR14.


32 miles (51 km)
One hour without stopping or one full day to visit places along the way.
Main Roads:
CT-169 N
The only fees are at select attractions.

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