Connecticut Scenic Drives: Connecticut State Route 169

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 State 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 Roseland Cottage/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. 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.

Cultural Qualities of Connecticut State Route 169

The historic and cultural significance of this area was recently spotlighted by its designation as a National Heritage Corridor. The Quinebaug and Shetucket Rivers Valley National Heritage Corridor (Q-S NHC) recognized the great potential for recreation and site interpretation due to the byway's abundance of outstanding 19th-century mills, mill villages, and beautiful landscapes. State Route 169 forms the western edge of the Q-S NHC and is considered an important element in the Heritage Corridor, especially as a means for linking its many diverse historic sites.

In addition to two National Historic Landmarks (Prudence Crandall Museum and Roseland Cottage), there are more than 175 historic sites and districts recognized by local and state surveys and/or the State or National Registers of Historic Places. The National Register of Historic Places lists two districts along State Route 169 (Bush Hill and Brooklyn Green, both in Brooklyn), as well as individual properties. The rich architectural heritage of villages, such as Brooklyn, Pomfret, and Woodstock, is representative of the hill town communities that settled this part of Connecticut and are still very much intact.

Qualities of Connecticut State Route 169

The history of this ancient road is inextricably tied to the history of the hill towns of northeastern Connecticut. Since prehistoric times, the route has wound its way along, up, and down the spines of age-old hills in a north-south direction. Windham County historian Ellen Larned tells us that a Nipmuck Trail ran from Wabbaquasset (i.e. the Woodstock area) to the seashore. If some parts of that trail and today's State Route 169 are not the same, there were undoubtedly footpaths of American Indian origin that took much the same course. On the northern end, it seems certain that John Eliot and Daniel Gookin crossed portions of this route in 1674 as they made their way to what is now Woodstock. During the decade that followed other people made forays into Wabbaquasset territory, burning cornfields and American Indian forts. It is only logical to assume that they used American Indian trails and perhaps some part of what is now State Route 169.

The first improvements by Europeans most likely occurred after the settling of Norwich in 1659; Lisbon was then a part of Norwich. However, the course of the lower portion of the highway was changed sometime after 1854, detaching the most ancient part of the road in that region. At present, there is no documentation for the road at the southern end.

At the northern end, the Proprietor's Records of Woodstock record the laying of a road from North Running Brook, north of the village of Woodstock, to Sawmill Brook, in South Woodstock, by the first "Goers" during the summer of 1686. The public right-of-way was eight rods wide in some parts, and six rods wide in others (the rod used was probably 11 feet). This was quite a large width considering it was used primarily for foot traffic, occasional teams of oxen, and riding horses. This width allowed for common lands on either side of an improved, traveled way.

Follow this map of Connecticut State Route 169.

The Woodstock portion of the Norwich and Woodstock Turnpike was made free in 1836, while the rest of the road remained a toll road for another ten years. In 1846, the corporation persuaded the Connecticut assembly to relieve it of its obligations on the grounds that the cost of the road had been more than 14,000 dollars and that no considerable profit had ever been realized. Since the operation of the Norwich and Worcester Railroad, the income had not been sufficient to provide for the necessary repairs and no dividends had been paid for six years. Consequently, the railroad was blamed for the demise of the 19th-century turnpike era.

Railroads also had other effects on the hill towns. To Pomfret, where the railroad passed over the highway, it brought summer tourists and a grand way of life; to other towns bypassed in favor of the thriving mill towns along the Quinebaug, it brought a long, slow decline. The period of dormancy is in large part the reason why so much of the path of this historic highway has remained unchanged throughout the years. As for the Norwich and Woodstock Turnpike, it undoubtedly remained much the same until the advent of the automobile and the development of the state highway system in the 20th century, when it was first given the number 93, which was later changed to 169.


Early photographs are plentiful, showing portions of the road as a narrow, graded, and crowned dirt road. It has grown somewhat wider through the years, has been blacktopped along its entire length, and in recent years has been very well maintained. Even with all these improvements, one can still feel the bumps and turns of the ancient road, see the horizon ahead disappear and reappear, and feel a continuity through time with all who have traveled this beautiful road.

Qualities of Connecticut State Route 169

The spectacular views that travelers witness from State Route 169 are owned by the thousands of individual property owners that live along the corridor. The attractive pattern of land use that has evolved over many centuries is the result of the individual actions of the residents of the five towns that the corridor traverses. State Route 169 traverses the physiographic region of Connecticut known as the Eastern Uplands. Within the eastern uplands there are three distinct landscape types: Glacial Till Uplands -- the ridge tops and side hills, Drumloidal Glacial Till Uplands -- the more rounded and oval shaped uplands, and Glacial Outwash Plains -- the bottomlands.

These three landscape types form a subtle impression upon the visitor to northeastern Connecticut, and a visit along State Route 169 traverses all three. Starting from the south, the route parallels the Quinebaug River bottomlands, barely skirting the side hills until just north of Canterbury. Here the road intersects a drumlinelike formation, and then it descends back down into the bottomlands associated with Blackwell Brook. Just north of Brooklyn, the road starts to climb again across glacial till uplands, and then it reaches what is sometimes referred to as the Woodstock Drumlin Field.

The most visible landscape type comes from the view of the immediate roadway environment. This includes the close landscape of the villages, woodlands, and farmsteads adjacent to the road. This intimate setting, often framed by stone walls and mature lines of trees, is the most memorable experience along State Route 169, and this is one of the few areas where this type of southern New England landscape remains intact. The stone walls found along this route are the result of hundreds of years of agricultural development, and in that sense, the walls are irreplaceable.

The network of streams and wetlands found throughout the corridor also add to the beautiful scenery and natural qualities of the byway. Waterways such as the English Neighborhood Brook play throughout the long-distance vistas and the mature tree canopies on the route. Many of the lands and waters that compose this system of wetlands and waterways are already protected by existing floodplain and wetland ordinances, creating a backbone of greenways and open spaces that help to embrace and separate different uses of land.

Within the scenic views along State Route 169 are extensive areas of woodland. Many of these areas have avoided agricultural use to become mature woodland as the agricultural economy has been transformed from farming to manufacturing to a service-sector orientation. These woodlands continue to play an important role in the way both visitors and residents alike perceive the character of the corridor. The highly visible wooded hillsides that provide a particularly attractive setting for the towns and villages along State Route 169 are a main characteristic of the drive. When combined with the attraction of fall color, these wooded hillsides are even more enticing.

Find more useful information related to Connecticut State Route 169:

  • Connecticut Scenic Drives: Connecticut State Route 169 is just one of the scenic byways in Connecticut. Check out the others.
  • How to Drive Economically: Fuel economy is a major concern when you're on a driving trip. Learn how to get better gas mileage.


Highlights of Connecticut State Route 169

© Historic architecture is abundant along Connecticut State Route 169.

As visitors drive Connecticut State Route 169, they are taken on a tour of provincial Connecticut with all its natural and cultural charm. The scenic qualities of the road are further enhanced by the extraordinary number of antique 18th- and 19th-century structures that have survived along the whole length of the highway.

Each town and village along the way has its own subtle, unique character in the buildings and people that live there. Between villages, the north/south running ridges of hills provide frequent vistas, sometimes in two directions, and a gentle, undulating path of travel. The natural flora is mingled with a still viable agricultural heritage, delighting the eye with changing patterns.


The wooded hills are covered with many varieties of trees and shrubs, including some giant and very old trees of varied species. These trees fade into vast cornfields and occasional wooded areas that come right to the edge of the road to envelop travelers with a sense of deep forest and life. Travelers also see well-groomed hay fields, picturesque apple orchards, rustic farm scenes, and an abundance of wildflowers.

The catalog of delights to be found along the road is endless. Beneath a canopy of tall trees, each village has a significant number of early houses, one or more churches, a library (often in an antique building), a grassy common or green, and all the other features thought of as New England. In the villages, or along the road, visitors will find graveyards with carved gravestones dating from earliest times. Students of gravestone carvers come from all over the country to see the stones found in this region.

Lining the edges of the roads are stone walls of amazing variety and fences and gates. If travelers wish to stop and leave their cars, they can see and hear countless species of birds, insects, and other fauna and rare wildflowers. All of these are free for any who come and look. For those who wish to shop a bit, there is an assortment of gift shops, good restaurants, and very pleasant bed-and-breakfast accommodations.

One extraordinary feature of this byway is that there is so little intrusion of commerce, industry, or development along the route. Nowhere along the 32 miles is there a stretch more than half a mile in length that can be said to be dull or unsightly. As of this date, there is not one strip mall, and the only modern office buildings of more than one story are the Woodstock remnants of a defunct college. These are in a lovely, parklike setting that is now owned by Data General. About a mile away, Linemaster Switch, one of the largest employers in Woodstock, has a large frontage property on the road with not a single building in view.

Though only a brief distance, this scenic byway is long on history with charming villages dating back more than 300 years. This itinerary covers some of the natural and historic highlights of your journey along Connecticut State Route 169 as you travel from north to south.

Roseland Cottage: Begin at the Roseland Cottage/Bowen House Museum in Woodstock. This home with Gothic Revival architecture was constructed in 1846 and hosted elegant summer soirees attended by the elite of the day, including numerous Presidents. Containing original furnishings, bowling alley, and garden, guided tours are available on the hour.

Connecticut Audubon Center: Though Pomfret has many historic churches and homes, it is the natural features of the area that are highlighted at one of northeastern Connecticut's newest attractions. The Connecticut Audubon Center is a new nature center that offers educational programs and bird walks. It is also the gateway to the adjoining 700-acre Connecticut Audubon Bafflin Sanctuary.

Brayton Grist Mill and Marcy Blacksmith Museum: Just west of Pomfret on Route 44 is the Brayton Grist Mill and Marcy Blacksmith Museum, located at the entrance to the Mashamoquet Brook State Park. It is an 1890s mill with the original equipment. The Marcy Blacksmith Museum has exhibits that detail more than a century of blacksmithing and three generations of the craft.

Mashamoquet Brook State Park: This park offers camping, hiking, and picnicking. The most famous feature is the Wolf Den into which, on a night in 1742, Israel Putnam crept and shot a wolf that for years had preyed upon local sheep and poultry. Putnam later gained fame as a major general in the Continental Army during the Revolutionary War. Near the Wolf Den are the Table Rock and Indian Chair natural stone formations.

Brooklyn Historical Society Museum: This museum houses a collection of 18th- and 19th-century artifacts and Brooklyn memorabilia. Additionally it features historic items about the life of Revolutionary War hero Israel Putnam and special annual exhibits. The law office of Putnam's great-grandson, Daniel Putnam Tyler, is also open to the public.

Putnam Elms: Yet another Putnam family site is Putnam Elms. Constructed in 1784 by the Putnam family and still maintained by Putnam descendants, the house is open for tours and contains exhibits about the history of Colonel Daniel Putnam and his father, General Israel Putnam.

Finnish American Heritage Hall: Built in the 1920s, the Finnish American Heritage Hall in Canterbury is not only a social hall for those whose families immigrated and contributed to the melting pot of America; it is also the site of the Finnish American World War II memorial dedicated to Americans, including all the Finnish Americans, who fought in the war. On April 10, 1998, the Finnish Hall, along with numerous other buildings and residences on the Canterbury Green, was entered onto the National Register of Historic Places.

Prudence Crandall Museum: This museum is located on the site of Prudence Crandall's home, the first academy for black women in New England. Crandall's activities were not without controversy. Admitting Sarah Harris, a young black girl, to the women's academy outraged parents and townsfolk and caused an angry mob to ransack the school. Fearing for the safety of her students, Crandall closed the academy. Today this National Historic Landmark features three period rooms, changing exhibits, and a research library.

John Bishop House: At the end of the byway the John Bishop House in Lisbon was built in the early 1800s. The structure features doors that are butt-hinged, nails that are machine cut and headed, and a framed ridge in the attic. The house also has seven fireplaces. A shaftway leading from the buttery down to a dug well, where water could be obtained without leaving the house, is a unique feature.

Connecticut State Route 169 winds its way through the best in Connecticut history past Colonial homesteads, churches, stone walls, covered bridges, and quaint museums as it connects several classic New England towns.

Find more useful information related to Connecticut State Route 169:

  • Connecticut Scenic Drives: Connecticut State Route 169 is just one of the scenic byways in Connecticut. Check out the others.
  • How to Drive Economically: Fuel economy is a major concern when you're on a driving trip. Learn how to get better gas mileage.