Here's a YouTube playlist of these songs for continuous listening)
GEORGE JACKSON & LINDA LUCCHESI - It's Hard To Say No
George is a southern soul legend, having written songs for greats like Wilson Pickett, Candi Staton and James Carr in his day. This beautiful, albeit low fidelity, stripped-down demo captures him at his most earnest and tender.
Fred Redden - The Banks of Claudy [Folkways, 1956]
A classic Celtic folk song about longing for home & family after embarking to Australia, recorded near the banks of Nova Scotia - interestingly, despite the subject matter of the well-known version, very few Australian recordings of the song exist. A pining, moving account of nostalgia.
CATHIE O'SULLIVAN - Barbry Allen [larrikin, 1980]
A beautiful rendition of this classic Scottish folk tune by Australian harpist Cathie O’Sullivan. I had heard her later attempts at Reggae before, but finding her first LP for Australian folk label Larrikin was a revelation, it’s beautifully sung and wonderfully arranged Celtic folk music the entire way through.
FAIRPORT CONVENTION - Who Knows Where the Time Goes? [Festival, 1969]
One of the most beautiful, wistful songs Sandy Denny ever penned. One of the standouts on Fairport Convention’s classic “Unhalfbricking”. Her version recorded with the Strawbs is also worth seeking out, recorded 2 years before this, but unreleased until the mid-70s.
DAVE BIXBY - Drug Song 
The haunting opening of Bixby’s private press LP “Ode to Quetzalcoatl”, this song has the somber mood and lyrical intensity that makes this singer-songwriter sound so personal and unique. After harrowing experiences with LSD and his eventual born-again faith, Bixby truly sounds like a broken man here.
ROBBIE BASHO - Rocky Mountain Raga [Windham Hill, 1978]
Best record on Windham Hill by a country mile! Basho’s mesmerising guitar playing and unique, powerful voice is accompanied by a violinist on this incredible piece, a misty eyed vision of the Rocky Mountains.
STUDIO DER FRUHEN MUSIK PERFORMING PERTER ABELARD - Planctus David [EMI/Reflexe, 1974]
Abelard was an 11th century poet and composer - this “Planctus” is a lament, rendered here by early music group Studio der Fruhen Musik. An incredible, otherworldly piece of music guided by incredible vocal and instrumental interplay - a nice introduction to early music for those who cannot hang with the economy of a lot of vocal music.
YOSHI WADA - Off the Wall [FMP, 1985]
Wada is an artist and Minimalist composer who studied with Pandit Pran Nath, and created many works based around loud, extended drones that filled the room with harmonic overtones. This piece for legendary Free Improv concern FMP was recorded with a quartet and sounds immense!
MORTON FELDMAN - Crippled Symmetry [Hat Aart 1991]
I remember attending a performance of this in Brisbane, about 3 years ago, this time of year - multiple people fell asleep during the piece! Beautifully mercurial and shifting in structure, with a beautiful, crystalline clarity to the playing, this is a great entryway into Feldman’s oeuvre.
PAYSAGE D'HIVER - Gefrorener Atem [Kunsthall Produktionen, 1999]
Black metal is perfect music for winter! This Swiss band trade in a particularly melancholy, frostbitten brand of black metal that lacks some of the aggression of a lot of their contemporaries. Their name translates as “Winter Landscape”, and their music definitely conjures up the wintry climes of the Alps.