The Churchill–Roosevelt Highway is the major east–west highway on Trinidad island in Trinidad and Tobago.

It runs for 30 km (19 mi) from Barataria in the west (where it joins the Beetham Highway) to Wallerfield in the east (south of Arima) where it ends in the former US Army base on Fort Read. It crosses the north–south Uriah Butler Highway (UBH) at Valsayn. Constructed during World War II to connect the US Army base with Port of Spain, the highway was named for the two wartime leaders, Winston Churchill and Franklin D. Roosevelt.

Construction began in December 1941 and was completed in March 1942. Originally reserved for the US armed forces, the road was turned over to the Government of Trinidad and Tobago on October 24, 1949.

The Churchill–Roosevelt begins at the Barataria interchange, where traffic from Lady Young and the Beetham join. The highway then passes south of San Juan and through the El Socorro and Aranjuez area. It has a massive, congested intersection at El Socorro Road. In order to relieve the situation, a new interchange is being constructed to replace the present intersection. Further east, the congestion with UBH at Valsayn has been alleviated by a brand new flyover. The Churchill–Roosevelt continues east pass St. Augustine, Tunapuna, Tacarigua, Trincity, Arouca, Maloney and Mausica before narrowing to two lanes. After this, it circles the town of Arima and ends soon after.

When WWII commenced, Trinidad became an important strategic point in the war effort. Through the Bases Agreement signed by British PM, Sir Winston Churchill, and the US President, Franklin Delano Roosevelt, Britain got 50 old American destroyers, and the US was granted the right to establish bases in the British Territories. Although the US Army had several bases on the island by 1941, the most important were Chaguaramas and the Air Base at Wallerfield, called Fort Read. The road communications between the Port of Spain (POS) and Fort Read near Cumuto was problematic as it consisted solely of the crowded Eastern Main Road, which slowed down the large convoys moving between the two bases. The decision was made in 1941 to build a military two lane paved road between Fort Read and the Morvant Junction of the Eastern Main Road just outside POS (the extension of the highway, the Beetham Highway, would not be built until the 1950s.)

Work began almost immediately, with the highway forever bisecting rural communities like St. Augustine, El Socorro and Tacarigua. Many crop farmers had to be moved as bulldozers ploughed the course. This era in history is documented in Samuel Selvon’s classic novel, A Brighter Sun, where an inexperienced Indian youth is thrust headlong into the highway-building process. When the road was opened in 1942, it was the finest road in the island, being smooth and pothole free from end to end. It was not immediately asphalted, as it was pressed into service for the convoys almost as soon as the way was graded (a stark contrast to our roads today). Wilson Minshall, father of masman Peter Minshall, remarked “The new Roosevelt–Churchill Highway has swept across the country from Cumuto to a point near Laventille with the force of a flood rushing into a quiet valley. Cleared and graded but not yet surfaced, its naked earth weaves and interweaves protesting patterns under the wheels of army trucks and construction tractors that cannot wait until the road is finished.

Opened in 1942 and reserved exclusively for military traffic, with exceptions being made for top-ranking civil service personnel. Military police in jeeps constantly patrolled the 15 mile road looking for violators, who most often were Indian peasants in mule and bull carts crossing the blacktop in their own good time while speeding traffic bore down on them; with several accidents having happened in this way.

The highway was finally opened up for civilian use on October 4th, 1949.

There are presently plans to extend the Churchill–Roosevelt to Manzanilla as a world-class four-lane highway.

The Ministry of Works and Transport has also set out a plan to expand the highway from the area of the Santa Rosa Park to the Arawak processing company.