Following the ‘Rutland Railroad Weekend’ which was held in April 1987 in Troy, N.Y. under the auspices of the Rensselaer Polytechnic Institute Railroad Club, RRHS began the tradition of holding an annual convention, which has been put on continually for more than 20 years. Popular meeting places have been the communities of Troy, Bellows Falls, Burlington, and Rutland; however the convention has also been held in Bennington, Malone, Ludlow, Ogdensburg and Brandon, to name just a few.
RRHS conventions traditionally are very informal affairs. Held on a Saturday-Sunday, the first morning features a meet-and-greet, table vendors and a business meeting which is followed by a morning program, i.e., a power point presentation or guest speaker. The afternoon program is often an outdoor visit to a former Rutland facility or former customer(s), or could feature a train ride on the passenger equipment of the Vermont Rail System. A banquet is held on Saturday evening, followed by a guest speaker and additional entertainment. Plans for the second-day (Sunday) normally include a conducted auto-walking tour of a certain portion of the former Rutland Railroad (past examples have included portions of the Champlain Islands route, and the O&LC between Churubusco and Mooers).