I'll be working on this list over a period of time. These are what i consider a bit more obscure places (although not all are). I started with the two Nord territories (Bleakrock is a bad choice for most since if you've done the mq, the town is hostile)
THE RIFT:
Pilgrims Rest Inn, Ivarstead
-medium size, no functional chairs, minimal traffic
Tapped Vein, Shor' Stone
-medium size, party downstairs, small stage with entertainer, minimal traffic.
Riverside Inn, Nimalten
-medium size, benches for seating, no one goes to nimalten.
Nimalten Markets
-typical nord crafting area, no foot traffic, near riverside inn and the river.
Island e of Skald's Retreat
-small, romantic getaway, decent place to have a picnic or a clandestine meeting
Geirmund's Hall (east of Ivarstead)
-many npcs partying, quiet dining hall with no instruments/npcs, known by other rp'ers for being an empty place before homestead
EASTMARCH
Small farm between Old Sord's Cave and Icewind Peaks Dolmen
-house is break in, barn exists, few npcs. A place to perhaps have a meeting about delving or fighting against dolmens while overlooking the scenery in eastmarch
Winterland camp, south of Wittestadr
-an open camp with npcs that are yellow, meaning if you want to kill them you can
Small Camp outside the SW walls of Windhelm
-a good place to be planning illicit activities or to go out on a hunt
the abandoned camps from the new life festival
-the warming areas have some seating arrangements, the main tent is busier but less functional seating. No npcs there when the event is over.
Windhelm Docks
-a view towards Vvardenfell and some npcs, across from giants and mammoths in the town over. No big ships (unlike most docks/harbors)
This has been part one. I'll try to cover more in the future.