I can echo cujimmy's posting. Taking it from the Robin Hoods Bay side of Whitby starting on Church Street:-

The Middle Earth has sessions, sometimes just music, occasionally just singing.

The Fleece in past years used to have 2 or 3 seesions all day, however current licensees do not appear to have much regard for folk music but that might change for folk week and that tune beloved by landlords "The Old Rattlin' Till"

The Endeavour, programmed event of Maritime singing 1-3ish everyday then a free and easy session late afternoon and evening

Black Horse, one sometimes two sessions, very much a jump in session afternoon and evening, small venue which can easily be monopolised by a small group.

Friendship Rowing Club, free and easy sessions in an evening, big venue, cheap beer.

The Board, not always used but they do not mind someone starting in there.

The Dolphin, newly refurbished, folk friendly licensees but not used before, could be a good venue this year.

Baxtergate:-

Black Swan, used by folkies each year, sessions vary, depending very much on who gets in

Wellington, has been used in years past, dependent on people actually usung it.

Victoria Square

The Station, used all day music in the main bar and singing in the small room to the right of the front door. The same team use the small room each year and it is often difficult to get a seat never mind a song.

New Quay Road, the Ship, mainly music sessions all week, great for the diddly diddly lovers

Flowergate, the Elsinore has a session every week on a Tuesday night, that will probably be engulfed by folk week though, friendly enough pub that welcomes folkies.

York Place, bit off the beaten track up behind the hospital but there should be good sessions up there afternoons and evenings

There may be other session that I've overlooked, apologies to their afficionado's. A cracking way to get into Whitby is down the coastal path from the Bay, lovely walk, cliffs on one side of the path and beautiful rolling countryside inland.