Boston is a great town to ride in, but it's not a particularly cyclist-friendly city.

The city adiministration has a long tradition of wishing cyclists away. In fact, they laid off their bicycle coordinator several years ago and haven't bother refilling it since, despite substantial public demand.

There is a dearth of on-street bike parking downtown (though a good amount of it in garages if you know where to go).

The cops don't even know the rules regarding cycling on the streets. There are some bike cops, though. You'll know them because they're the ones riding on the wrong side of the street or on the sidewalk.

Enforcement is completely arbitrary. If you're a messenger, you'll get cited for not wearing a helmet...if the officer doesn't like you. On the other hand, that same officer won't even give you a second glance for running a light.

Motorists here often don't understand how to behave around cyclists.

The transit authority makes up excuses for not installing bike racks on buses. In fact, of the three routes that did have racks, at least one has mysteriously lost them. Though I've heard that the new GM is interested in working with advocates.

The traffic department has historically refused to even consider share the road signs because they were "too expensive". (Also a lie.)

In 2000, the city won the dubious double distinction of being awarded the title of America's least bike friendly city as well as having the Cycle Messenger World Championships relocated to Philadelphia following the railroading of a messenger who ran into a jaywalking pedestrian. Additional arbitrary courier regulations were enacted and the police force would harrass anyone they suspected might be a messenger.

The list could go on.

However, having said all that, it's a small, dense, and congested city. While the latter half of the 20th century damaged us as like any American city, it was less severe. Most of the city is well-connected by streets with traffic signals, on-street parking, retail destinations, and substantial foot traffic. This makes for a naturally traffic-calmed environment. The congestion tends to make the speed differential between cyclists and motorists less pronounced.

It's also true that the city seems to be changing its mind. The obvious support for reinstating the bike coordinator position as demonstrated at a public hearing last year seems to have lit a fire. They're solidly behind the upcoming Hub on Wheels festival and we've got someone on the inside at the BTD trying to work out a pilot signage project.