20 miles; from Route 2 in Norwich to RI 3 in Austin, R. I. 16.01 miles in Connecticut.

A rock formation along Route 165 in Voluntown is painted like a dog in this photo taken in 1940. Credit: Library of Congress, Prints & Photographs Division, FSA-OWI Collection. larger photo

Commissioned in 1932, the modern Route 165 originally ended at Route 138, taking the future Route 201 (I think) past Patchaug Pond. By 1936, it was straightened out, but still ended at the 138/49 junction in Voluntown. By 1940, it had its current general layout.

In the late 1950s, a section of Route 165 in Norwich and Preston was relocated slightly to the north. Long Society Rd. is the old alignment.

• Route 165 Ends (Photos; Doug Kerr at state-ends.com)

1.62 miles; from Route 153 in Westbrook to US 1 in Old Saybrook. Route 166 is the shortest signed state highway to cross a town line.

In the 1920s, State Highway 166 followed today's Route 30 between Route 74 in Tolland and Route 190 in Stafford.

Route 166 was commissioned in 1935. In 1962, during the state highway reclassification effort, Route 166 was proposed to be decommissioned and turned over to the towns. However, local officials persuaded the state to keep the route.

• "New Area Roads Discussed by Assembly Committee." New Haven Register, March 6, 1963.

• Route 166 Ends (Photos; Doug Kerr at state-ends.com)

10.41 miles; from US 202/Route 10 in Simsbury to Route 4 in Farmington. It intersects US 202 twice, though this is mainly 202's fault.

In the 1920s, State Highway 167 followed today's Route 151 between Routes 66 and 149.

Commissioned in 1932, the modern Route 167 has seen few or no changes since then.

CT 167: US 202?

In Avon and Simsbury, US 202 overlaps two other highways -- US 44 and Route 10. In January 1978, Avon officials explored moving the US 202 designation to Route 167, to divert some traffic from the town center on US 44. Route 167 would have kept its designation south of US 44, but would have become part of US 202 north of US 44.

Simsbury's agreement would be needed before the renumbering process, which could take up to a year, could begin. Simsbury officials were concerned about increased traffic past the town's high school, located on Route 167.

The move to change US 202's designation was eventually tabled.

• "Rerouting Decision May Take Year." Hartford Courant, Jan. 28, 1978.
• "Highway Proposal May Be Rejected." Hartford Courant, Feb. 4, 1978.

• Route 167 Ends (Photos; Doug Kerr at state-ends.com)

9 miles; from Route 75 in Suffield to US 202/MA 10 in Congamond, Mass. 7.93 miles in Connecticut.

In the 1920s, State Highway 168 followed today's Route 87.

The original Route 168, commissioned in 1932, connected US 5 and Route 17 on what is now Route 22; it became part of 22 in 1951, to help guide motorists from the Wilbur Cross Parkway to US 1.

The modern Route 168 was originally part of Route 190, which extended west to US 202/MA 10. The numbering was switched in 1977, to avoid conflicts between state route 190 and Interstate 190 in Massachusetts.

• "Route marks planned on links to parkways." Bridgeport Sunday Post, April 22, 1951.

• Route 168 Ends (Photos; Doug Kerr at state-ends.com)
• MA 168 (Dan Moraseski)

49 miles; from Route 2 and Route 32 in Norwich to US 20 in Charlton, Mass. 38.25 miles in Connecticut.

Route 169 is Connecticut's most prestigious scenic road, after the Merritt Parkway. Both have nationwide prominence.

The Danbury News-Times writes:

Route 169 follows the old Norwich and Woodstock Turnpike, which was incorporated in 1801. In 1846, the corporation reported that it was losing money and had paid no dividend in six years, partially because of opening of the Norwich and Worcester Railroad a decade earlier. At this time, the corporation was relieved of obligation and the road was made free.

The original Route 169, commissioned in 1932, ran along what is now Route 27, and was absorbed into 27 in 1951.

The modern Route 169 was originally called Route 93, which was also commissioned in 1932. The number was changed in both Connecticut and Massachusetts to 169 in 1959, to avoid conflicts with planned Interstate 93.

• Wood, Frederic J. "The Turnpikes of New England." Pepperell, Mass.: Branch Line Press, 1997. (reprint of 1909 edition)
• "Route 169 makes national scene." Norwich [Conn.] Bulletin, Mov. 13, 1992. (Thanks to the Lisbon Historical Society)
• "Road is trip to yesteryear: Scenic Route 169 shows off the beauty of eastern Connecticut's countryside." Norwich [Conn.] Bulletin, Aug. 4, 2003. (Thanks to Wm. F. Yurasko)
• "Scenic designation means road is special." Norwich [Conn.] Bulletin, Aug. 4, 2003. (Thanks to Wm. F. Yurasko)

• The National Scenic Byways clearinghouse Route 169 page
• MA 169 (Dan Moraseski)
• Route 169 Ends (Photos; Doug Kerr at state-ends.com)