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- 2007 Fall Colours Charter: TTC 4500 - October 21, 2007
- TTC Classic Charter: TTC MCI Classic 6292 - September 15, 2007
- Brampton Transit Classic Charter and visit to Halton County Radial Railway - May 27, 2007
- 2006 Christmas Lights Charter: Burlington Transit 7047-82 - December 16, 2006
- 2006 Transportation Weekend Charter: TTC Triple Header Trolley Charter - September 3, 2006
- 2006 Transportation Weekend Charter: HSR Artic Double Header - September 2, 2006
- York Region Transit 30-Foot Orion Double Header Charter - April 29, 2006
- 2005 Fall Colours Charter - October 22, 2005
- Ray Neilson Memorial Charter - October 1, 2005
- TTC 4500 Charter - September 18, 2005
- 2005 Ontario East Charter - May 7, 2005
- 2004 Christmas Lights Charter using TTC Orion VII 7617 - December 11, 2004
- TTC Orion V "CNG" Charter - October 23, 2004
- TTC Triple-Header Streetcar Charter - September 5, 2004
- Brampton Transit Double-Deck Charter - September 4, 2004
- Grand River Transit Charter - May 1, 2004
- TTC 6621 Christmas Lights Charter - December 13, 2003
- TTS 30th Anniversary Charter - September 21, 2003
- York Region (YRT 914) Charter - June 7, 2003
- Mississauga Orion I 8610 Charter - April 26, 2003
- 2002 Transportation Weekend Charter: TTC 4500 - September 1, 2002
- 2002 Transportation Weekend Charter: TTC 6259 - September 1, 2002
- 2002 Transportation Weekend Charer: GTA West - August 31, 2002
- Durham Region Charter - April 6, 2002
- TTC 2603 (ex-Montreal "Fishbowl") Charter - October 20, 2001
- York Region Charter - November 25, 2000
- 2000 Transportation Weekend: PCC 4549 Charter - Septmeber 3, 2000
- 2000 Transportation Weekend: Grand River Charter - September 2, 2000
- Farewell to GO Transit's "Fishbowl" Charter using GO Transit #1122 - April 29, 2000
- TTC "Fishbowl" 8051 Charter - March 25, 2000
- Tour of the TTC's Harvey and Duncan Shops - March 15, 2000
- TTC PCC 4500 Charter - October 30, 1999
- Niagara Region Charter using Greater Hamilton Tours MCI Classic #2207 - September 18, 1999
- Hamilton Street Railway GM Articulated #8201 Charter - June 13, 1998
TTS Members are invited to submit charter photos for posting here. Email the webmaster for arrangements.