Most Egregious Impediments to/Gaps in Walking around Boston?

But it would seriously interfere with the Charles River Basin's use for sailboats.
 
I wish the access to the Chelsea Street bridge was better on the East Boston side. 1a and the abanoned train track pit are in the way.
Charlestown to Chelsea -- was once possible before the old low-level drawbridge was replaced by the Tobin. They should have kept the drawbridge after the Tobin opened.
It would be cool to have a pedestrian only draw bridge there that would open and close for ships. I would definitely use it to bike from Chelsea to Boston because now I have to go through the food market and around to 99 which sucks. Unfortunately I don't know if it would be used enough in general to justify it. The fishermen would like it.
 
I may have mentioned this somewhere else, but I think a new Charles River pedestrian/bike bridge from Kendall to Back Bay (Wadworth to Clarendon) would be an extremely useful and well-travelled connection.

Similarly, we could take a cue from London (or rather, Greenwich).
 
The reason Dartmouth street is so wide, use to be a two way, was becuase the oroginal plan was to have a bridge into Cambridge.
 
There are so many of these annoying hurdles in Boston. A lot of them are due to the Pike and Storrow Dr.

Some other notably frustrating examples:

The closure of Dot Ave at the Postal Annex that cuts off the most direct route from the FiDi to S. Boston.

Trying to get from South Station/Leather District to the Broadway Bridge is an impossible nightmare.

Trying to get from the Muddy River into Brookline. This may change if the Carlton St Footbridge is ever restored.

Trying to get from the area of the Pru Mall by the Sheraton entrace to Boylston. There should definitely be a public access way through the Hynes. In a lot of other cities, public buildings are actually public.

Trying to move between the SWC Park and St Botolph between Mass Ave and W. Newton. Why do streets like Albemarle and Blackwood dead-end rather than connect to the park?

I agree with most of those already mentioned, especially Stuart between Dartmouth and Huntington which is an absolute disaster.

I may have mentioned this somewhere else, but I think a new Charles River pedestrian/bike bridge from Kendall to Back Bay (Wadworth to Clarendon) would be an extremely useful and well-travelled connection.

This one is screamingly obvious. I wonder why this idea gets so little attention.

There also really really needs to be a pedestrian connection to E. Boston.
 
Trying to get from the Muddy River into Brookline. This may change if the Carlton St Footbridge is ever restored.
There are a lot of people in Brookline clutching at their pearls right now thinking about this. They don't want to make it easier for people from Boston to get into their fancy suburb, at least not from that direction.
 
The whole mess of roads just north of Harvard Square. Just try walking north on the eastern side of Mass. Ave. Even on the other side, there's a curb cut at the bottom of Cambridge Common that's a death trap when drivers don't stop for pedestrians...they barrel through and there's no signage or signaling to indicate what to do whatsoever.

Even Harvard Square itself has problems, notably the curb cuts around Brattle Square and the lack of signaling for crosswalks on Brattle and Eliot Streets.
 

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