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This dead-end section of Somerset Street, next to the Portland Flea for All, is one of many minor nuisances to walking and cycling in the growing Bayside neighborhood. This particular one is located at the western end of the new Bayside Trail, and is one of the reasons that particular pathway is currently so little-used. The street seems to have been disconnected as part of the urban-renewal-era effort to turn Preble and Elm Streets into high-speed, one-way auto expressways.
Thankfully, that's about to change. The city has just put out a request for bids to re-connect Somerset Street across Preble and Elm, and to study possible routes to extend Somerset Street as a bike and pedestrian route all the way to Forest Avenue and Deering Oaks Park. Part of the study component of this project is expected to look into the possibility of making Preble and Elm back into two-way streets, and opening up new redevelopment opportunities on adjacent blocks — possibly something like this.