Most Inspirational Music Albums of All Time (Inspired by the Seasons)

Music provides the backdrop to our lives. We each have our own personal soundtrack. Be it from songs that affected us due to the lyrical content, have us recall deep memories or simply bring us back to a certain time or place in our lives.

Since my first year in college (2001), I have made compilation albums of the tracks that shaped the last few months. It could be songs that I especially liked, heard often or became connected to in some other way. When I listen to these mixes, I am back in my dorm room in Boston or driving to my summer job in Mystic, Connecticut or even more recently, watching my son smile at me for the first time. Each track holds deep meaning for me.

Time and time again, I reach for certain albums or specific tracks when the weather changes. The following is a checklist of the music that has seasonally inspired me. Due to the fact that the weather is (finally) beginning to warm up here in the northeastern United States, I’ll start with the summer playlist and work around the calendar.

Artists, songs, and albums are chosen here purely because they have been inspirational to me or reflective of the season. This is not a comprehensive list of the most popular seasonal music, but simply ones that have shaped my life.


Bruce Springsteen – Greetings from Asbury Park, N.J.

There is no question that Bruce evokes vivid memories. Songs such as “4th of July, Asbury Park (Sandy)”, “Highway Patrolman”, or “Born to Run” make you feel that you lived these songs. Bruce’s first, Greetings from Asbury, N.J. to me represents being young in the summertime.

As songs such as “Spirit in the Night”, “Blinded by the Light” and “Growin’ Up” recall carefree summer nights with friends before life had real responsibilities. For me, this cassette tape was played with the windows rolled down, just a little too loud as I cruised down the highway heading towards a New England beach town on one of those first warm days of June.

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Cracker – Big Dipper from The Golden Age

The lyrics in this wildly vivid track even namecheck “ those sleeveless days of June.” The protagonist’s plight, hanging in town watching the girls walk by and whiling away the hours, “sitting on the cafe’s inner steps with a book he hasn’t started yet”, feels familiar to us all. It’s the perfect summer scenario, one that as I grow older, one that I increasingly romanticize.

George Winston – Summer

It is truly amazing what emotion Winston can convey with just a piano. Similar to his other seasonally themed albums, Autumn and December, the music on Summer, along with its apropos cover art of a field under the fading light of the afternoon, truly embodies the season. From the upbeat “Living in the Country” to the laid back vibe of “Loreta and Desiree’s Bouquet Part 1” to the meditative “Spring Creek”, this album hits on the many facets of the summer season.

Jonathan Richman – That Summer Feeling from Jonathan Sings!

Jonathan’s storytelling is on a higher level in my opinion with Bruce Springsteen and Tom Waits. Listening to “That Summer Feeling”, which romanticizes past events “that summer feeling is going to haunt you the rest of your life”, “when even fourth grade’s looking good, which you hated, and first grade is looking good too, overrated” describes perfectly the human emotion of longing for the past when it is no longer attainable.

Chris Isaak – Baja Sessions

This album IS summer! Who cooler than Chris Isaak to bring you a breezy foray into island time? The beach, the sun, long summer nights. This is the perfect backdrop for a romantic evening under the stars. The album is mostly reworked Isaak classics and cover songs. From the first notes of “Pretty Girls Don’t Cry” and the listener is transported to a perfect summer night. For years, this album has epitomized that perfect evening. This album and San Fransisco Nights are two of his most summer-centric albums.

Red House Painters – Ocean Beach

Mark Kozelek, leader of Red House Painters, is one of my favorite artists. His work, with RHP, later in Sun Kil Moon, solo and with collaborators is always striking. From his earliest tracks in which loneliness and loveliness collide with stark but breathtaking results to his latest releases that detail his thoughts on such a thorough degree, and explores all aspects life, even and sometimes especially, the uneasy parts, like a lyrical Bukowski. Ocean Beach, with sad but beautiful songs such as “Shadows”, “Summer Dress” and “San Geronimo” was his first album to grab me. It brings me back to Cape Cod, summer 2002. To me, it recalls trying to grasp the fading days and last light of summer before the days sink to cooler weather. The longing in the songs is reflected in those perfect summer evenings that are spiked with a hint of sadness due to the fleetingness of the moment.

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Eva Cassidy – Fields of Gold from Songbird

Similar to Red House Painters album from above, Cassidy’s rendition of the Sting classic is modestly arranged, in this case just her and a guitar. Both too, are pretty but with a strong sense of yearning. The lyrics describing the summer days, with images of the sun and fields of barley, make it appropriate for the season.

Jonathan Richman – I Love Hot Nights from Modern Lovers 88

Only Jonathan could glamorize those sticky, sweaty hot nights in the middle of an August heat wave and make you wish you were there! “I’m just glad to see the lights downtown, smell the fried food and hang around” Richman has the uncanny ability to describe a sense of place in his music. In this track, not only is the listener transported somewhere, but we know what Jonathan is seeing, feeling and even smelling.


Josh Ritter – Homecoming from Sermon on the Rocks

“The nights are getting colder now, the air is getting crisp” These lyrics begin this monumental Ritter song setting the autumn scene. Whereas many of the summer songs it had a sense of sadness, this is a triumph. A return home, settling in and enjoying this moment.

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George Winston – Autumn  

This album brings me to a perfect fall day in New England. A blue sky providing a backdrop for the colorfully changing leaves. To me, this is the soundtrack of my rides up Route 169 in Connecticut. It is the taste of apple cider, the warmth of the sun on a cool day and the smell of burning wood in the distance. From start to finish it is the most serene and most perfect seasonal album. Take the first song “Colors/Dance”, each note of the piano is the sound of each leaf changing colors and then falling.

Paolo Nutini – Autumn from These Streets

The first song on this album “Jenny, Don’t Be Hasty” is what originally drew me to Paolo Nutini. I remember distinctly when I heard this track for the first time though, Columbus Day weekend pulling off the exit on my way back home. I took a few extra moments in the car to finish it before entering the house. The simple arrangement of voice and piano bring to mind the coming bareness of the trees.

George Strait – The Chill of an Early Fall from Chill of an Early Fall

Although fall is my favorite season, this song brings to mind that the fall is also a time of endings. In this case, a relationship, but it represents the feeling of being alone which can be synonymous with the season.

Cheryl Wheeler – When Fall Comes to New England from Driving Home

This song simply describes this awe-inspiring time of year in New England. It paints a picture of acorns, “Irish setter red” trees and stone walls, this is quintessential New England. For me, this is the perfect description of my favorite season in my home region.

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Richard Shindell- Are You Happy Now? from Sparrow’s Point

Breaking up is never easy but on Halloween? Shindell’s story song puts this couple’s private life on display in front of awaiting treat-seekers. He wakes up to find not only his relationship wrecked but also his home the next morning which makes the song even more depressing.

M. Ward – Poor Boy, Minor Key from The Transfiguration of Vincent

I read about the M Ward album The Transfiguration of Vincent long before he was a household name. I picked up the album and listened to it as I walked through the Back Bay of Boston to my apartment. The first track, “Poor Boy, Minor Key” sounds otherworldly. His whispered vocals and old creaky arrangements screamed November to me. This song represents the time period when the leaves are off the trees, a cold wind blows, and the skies are grey.


George Winston – December

The first track begins with “Thanksgiving” and the album takes us through the Christmas season, combining favorite recognizable songs such as the “Carol of the Bells” and Pachabel’s Canon with Winston original compositions. If Autumn represents a bed of fallen leaves, December is the soundtrack to a stark, moonlit field of snow and introspection during the Christmas season. Again, it is utterly amazing to hear the emotion expressed in Winston’s solo piano artistry. A classic for the holiday season.

Vince Guaraldi- A Charlie Brown Christmas 

This soundtrack is so much more than simply background music to a children’s Christmas special. Guaraldi’s jazzy, Bossanova inspired takes on Christmas classics such as (“O Tannenbaum”) syncs with the Peanuts ideal and that of the true meaning of Christmas. Simple and heartfelt, this album will always remind me of a snowy late November day driving through central Massachusetts. The anticipation of the coming Christmas season and the swaying rhythms of this album make it seem all is right in the world.

Joni Mitchell – River from Blue  

When the world is supposed to be full of joy with the Christmas season, sometimes it simply isn’t. Mitchell’s heartbreaking song tries to escape the holiday season. I think we’ve all been there.

Sufjan Stevens Sister Winter from Songs for Christmas and Christmas in the Room from Silver and Gold

Sufjan Stevens’ two five album boxed sets of Christmas music run the gamut from sad and quiet to grandiose and silly. Two of my favorite tracks are “Sister Winter” and “Christmas in the Room” which both echo a loving sentiment but with a tinge of sadness.

Tori Amos – Under the Pink

Great for those mid to late winter memories. Her haunting voice and stark, driving piano playing I always associated with the winter season. “Pretty Good Year” always makes me reflect on the past year when a new calendar is hung on the wall.

Chris Isaak – Winter Waves from MOM 3: Music for our Mother Ocean

This track has a dreamy, retro vibe most often reminiscent of the summer, but wait, the lyrics recall those winter waves. (Yes, the ocean is still there, even in the offseason!). This brings me back to studying for assessments in college, taking the subway to the Wonderland subway stop in East Boston, studying on the train and then near snow-covered Revere Beach bundled up on a sunny winter’s day.

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Frank Sinatra – In the Wee Small Hours

This record makes it seem almost “cool” to be lonely. It paints a blue portrait (just like the cover art). The endless, restless nights are similar to the bleak mid-winter when the first hint of spring seems an eternity away. From the first track, “In the Wee Small Hours of the Morning” through “This Love of Mine” it’s the perfect accompaniment to feeling alone.


George Winston – Winter into Spring

Yes, yet another Winston album, but his solo piano albums are so full of emotion and somehow capture the spirit of each season distinctly. “February Stars”, envelops the listener like a sky full of stars on a February night. As the album progresses, it culminates with “The Venice Dreamer part 2” which to me represents the thaw of the spring. The first instances of blooming flowers as color protrude through the recently snow-covered terrain.

Cliff Haslam – Silver in the Stubble  from The Clockwinder

Looking at yourself in the mirror and realizing that you are getting older, but still noticing the pretty girls as the weather warms. It’s a stark realization, and Haslam sells it perfectly. It is one of the many, many strong tracks on the truly great album, The Clockwinder.

Nick Cave and the Bad Seeds – Lime Tree Arbour from The Boatman’s Call

Maybe it’s the lyrical content, but this song has always had a special springtime feeling about it to me. The imagery of the loon, the wind in the trees, and the arbor show that love is renewed in the springtime.

Jonathan Richman – Springtime in New York from Her Mystery Not of High Heels and Eye Shadow

Simply one of the finest songs about the spring season. Richman describes perfectly those first warmish days of the spring in New York City detailing the sites, sounds and even smells that accompany this trip out of doors including that of a feuding couple and the remarkable line, “when demolishing a building brings the smell of 1890 to the breeze.” Enjoy this fleeting moment since the hot and humid summer is just around the corner.

Van Morrison – Astral Weeks

A truly mesmerizing album, any time of the year, but I’ve always associated with the rebirth of springtime, maybe since on the title track he repeats “to be born again”. Sit outside close your eyes and enjoy the breeze of the warmth of spring. It is best to listen to this album in its entirety, not simply one track or another. The long meandering songs are like the lengthening of the daytime with the coming of spring. Truly essential for any record collection.

I hope you’ve enjoyed this 365-day musical journey around the calendar.

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Website: Backyard Road Trips

Hailing from Norwich, Connecticut, Zachary Lamothe is the author of the Connecticut Lore book series released on Schiffer Publications. 

His own blog, explores family-friendly places in New England. Lamothe earned a bachelor's degree in American Studies from Boston University and a master's degree in Special Education teaching from Southern Connecticut State University. He has taught special education and history for many years. He lives with his family in Plymouth, MA. Look for his new book, A History Lover's Guide to the South Shore coming soon.