Provincetown was only accessible by boat or loose sandy roads until an extension of the Old Colony Railroad was completed in 1873, ending at what is now MacMillan Pier. Passenger service came to an end in 1940, but freight service continued until 1960. Harry Kemp Way now follows the original railroad bed, while 24 acres between Howland Street and Mayflower Heights are owned by the Town for conservation and passive recreation. Stone markers still exist near the Howland Street trailhead, indicating where a turn-around once existed for the trains. Other pieces of the railbed have been repurposed along the trail.

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Now a popular walking and bird watching area, Old Colony Nature Pathway is just under 1.5 miles long, alternating between sand and slightly packed dirt. There are other town conservation lands abutting the property, as well as a mix of pitch pine and oak forest, open dune, and freshwater swamp, including rare white cedar swamps.