I would break down the particular bike-friendliness of an area into two categories: culture and infrastructure.
In Worcester, it's hard to say whether the infrastructure is quite there yet, or whether it's pretty decent considering what it's like in other cities. I dnt have a heck of a lot of perspective, but compared to, say, Cape Cod, Worcester falls behind. But jeez the Cape is amazing. You can basically get to wherever you want to go mostly using dedicated bike paths. That's never going to happen in Worcester.
Worcester has it's end of the Blackstone, and there are random bike lanes here and there. Construction is supposed to start soon on an extension of the path up to Union Station, but that seems to be about it right now.
As far as riding a bike in the city goes, I find it easy and enjoyable. Take Mill Street, which I meandered down the other day. I was told recently that the wide shoulder was actually conceived as a bike lane. You wouldn't be able to tell, but there is one of those "bike route" signs. Bike lane or breakdown lane, it's very nice and long, and there's nice scenery to chew on.
Even in the thick of city traffic, it's not too bad. Chandler Street is a nice climb and a chance to pay respect to the place where it all started, Chandler Bike (it was still Barney's then, but technically it still is). Just under two years ago the Pug rolled out of there all nice and not shiny.
I think what I'm finding is that the infrastructure, quite simply, isn't as important as the culture. And right now, from where I pedal, that comes down to how drivers treat you.
And one of the revelations of my adventures in cycling in and around the city is just how expectation and stereotype-defying 99 percent of motorists are when I'm on a bike. Sure there are some bad apples, as with all aspects of life. Nobody and no city is perfect, and besides being the recipient of the odd yell out the windshield or having someone make a big show of how they're gunning it by you the first chance they get, I find that most drivers most of the time just give me the room or time I need, and pass by when they feel it's safe.
If anything, weirdly enough, some of my biggest peeves come not out of unfriendliness but of too much consideration. For example I don't like when people stop everything to let me turn. It makes me feel pressure to do so, even if I don't feel it's safe. And I also would rather a driver pass me closely, than leave some exaggerated wide berth around me. It makes me feel like I'm going to cause an accident.
So I guess I'd say that in my experience--obviously everyone's opinion is shaped by their own personal experiences--Worcester is a pleasant place to ride a bike.
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