Boston Post Road: Orange's Other Main Street
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Jim Dale Clothes, located on the Post Road and the Firelite Shop at the intersection of Old Tavern and Racebrook Road were fashionable clothing shops of the 1906s.
The name "firelite" harkens back to the time before the dress shop when it was a fireplace and accessories store. The sign for the shopping center has retained the original candle flame, which at one time was lit and moved. |

Peterson's Restaurant
This Amoco station was reportedly located in the vicinity of Dogwood Lane. Bud's Diner next door looks like another local eatery that took advantage of the heavy Post Road traffic.
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One of the more unique pictures of the Post Road is Gandy's Truck Stop located in the area now occupied by Party City. The ice loading dock in front of the garage was to manually dispense ice to the trucks both on top of the cargo and below.
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One of the most significant landmarks on the Post Road was that of the Wilson H. Lee Printing Company. It was erected in 1929 and equipped with the latest machinery for the production of high-grade printing. The tower was architecturally significant as well as functional, holding water used in the printing process. The location is now occupied by Home Depot.
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The Woodruff Tavern history goes back to the early days of the town built around 1767. In Enoch Woodruff's estate he left the house to his widow and the bar room to his daughter Polly with a large quantity of rum to his daughter Anne which suggests that the house may have been a public house before the Milford Turnpike (Route 1) was built in 1802. Its nickname of Half-Way House is derived from the distance between New York and Boston. In its prime the tavern was a popular place for lavish social events but by 1850 travel on the turnpike waned in favor of railroad transportation. In 1938 it was a boarding house providing bed and board for twelve people. Webster Bank is located on the former tavern property.