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Join Date: Aug 2010
Location: Madison, WI
Posts: 11,212
Bikes: 1961 Ideor, 1966 Perfekt 3 Speed AB Hub, 1994 Bridgestone MB-6, 2006 Airnimal Joey, 2009 Thorn Sherpa, 2013 Thorn Nomad MkII, 2015 VO Pass Hunter, 2017 Lynskey Backroad, 2017 Raleigh Gran Prix, 1980s Bianchi Mixte on a trainer. Others are now gone.
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I think that crank can't have a 2nd chainring added to it, so you would need a different crank to add more gears up front.
A five speed freewheel is 1970s vintage technology. If that is a Simplex rear derailleur, that would also be 70s technology. You might be able to fit a six speed freewheel to it, maybe a long cage vintage Suntour derailleur to get wider gearing if that freewheel was a wider range. Simplex gears had a fairly short amount of cable pull per shift compared to some other derailleurs, if it was setup with a vintage Suntour derailleur you might find that the shifter needs to move farther than desired to cover all the range of gears.
If the rear dropouts are spaced at 120mm, you might need a longer axle plus a spacer on that wheel to fit a six speed freewheel, you probably could fit a 126mm rear hub in that frame but it would take a bit more effort to pull the dropouts out a bit when you drop the wheel in.
If that is a 27 X 1 1/4 tire, those are getting pretty rare, most road bikes these days are 700c.
Interesting front light bracket on the fork. I have not seen anyone use those front wheel hub wing nuts since the 1970s, very retro.