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DISPATCH: Is it Bobby Brewster’s Woodshed or Doug Weston’s Troubadour?

Josh's manhandling of his acoustic-electric got caught up bopping back and forth with Keb’s blues wrapped in a Brit-Rock sound blanket. The absurdist game of ping pong they played will go down as legend — a cut scene for our very own Oregon Trail.
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Josh Ayala and Keb Hutchings-McMahon at the Woodshed in Brewster MA.
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TL;DR

Who performed at The Woodshed in Brewster on Monday night?

Josh Ayala played solo with a surprise guest appearance by Keb Hutchings-McMahon.

What kind of music was played?

A mix of acoustic folk, blues, classic rock covers, and original songs with improvisational flair.

What made this performance special?

The spontaneous collaboration between Ayala and Keb created a standout moment, capped with a blazing solo that had the whole crowd locked in.

When do Josh Ayala’s regular shows happen?

Every Monday night from 9:30pm to close at The Woodshed in Brewster; otherwise, he's up and down the Cape any night of the week - joshayalamusic.com

Is there video from the performance?

Yes! Two video clips from this legendary night is included below.

Why does this matter for Cape Cod music lovers?

Because the magic of spontaneous, high-level musical connection — especially with local names — is what makes the Cape’s live music scene so unique.

Post Summary

Who performed at The Woodshed in Brewster on Monday night?

Josh Ayala played solo with a surprise guest appearance by Keb Hutchings-McMahon.

What kind of music was played?

A mix of acoustic folk, blues, classic rock covers, and original songs with improvisational flair.

What made this performance special?

The spontaneous collaboration between Ayala and Keb created a standout moment, capped with a blazing solo that had the whole crowd locked in.

When do Josh Ayala’s regular shows happen?

Every Monday night from 9:30pm to close at The Woodshed in Brewster; otherwise, he's up and down the Cape any night of the week - joshayalamusic.com

Is there video from the performance?

Yes! Two video clips from this legendary night is included below.

Why does this matter for Cape Cod music lovers?

Because the magic of spontaneous, high-level musical connection — especially with local names — is what makes the Cape’s live music scene so unique.

Summer Mondays' Marathon Man, Josh Ayala, is in full residence @ the Woodshed in Brewster. “Mondays, 930-close” is how it’s billed. And if you manage to peel your suntanned thighs off the couch and get down to the Shed, you may just find a nickel under your pillow, like we did this week. Josh's manhandling of his acoustic-electric got caught up bopping back and forth with Keb Hutchings-McMahon's aired out blues, wrapped up in a Brit-Rock sound blanket. The absurdist game of ping pong they played out on Rockability Mutual Funds Memorial Field (nee The Woodshed) will go down as legend - a cut scene for our very own Oregon Trail.

Here's a taste - scroll to the bottom for the main course:

FTR

Understand, the weekly acoustic sets on that 6-inch stage are more enough to carry the evening. The melancholy-twinge and worn vinyl sound you’re expecting from the performer will bear down on you full bore - especially with Ayala recording new music for an album that he’s been heard to say will decide on which side 2025/26 its birthdate will be by the shape of the shape the leaves take in his bottom of his tea cup.

Catfish John rolls downhill into a Cripple Creek that sounds like it was shot half-full of New Orleans 40s jazz. Or The Band as an Andy Warhol collage, if Warhol chopped & squeezed the measures and skipped a chorus or three. The song's pared back to compact, and it's camouflaged - sometimes you just won't feel the timing coming. That's when you look the other way so the standard arrangement of the song can escape over the fence and be gone for good.

But this has had less to do with Doug Weston than with Bobby Brewster - and Doug Weston's is the name of the hour. Him and his version of a small club, the humble Troubadour.

Sure It's true that we do not have it on any authority that John Lennon & Harry Nilsson came bombing over from the Peacemaker to cause a scene but musicians out here are no different and musicians like to watch live music - so any number of local players may show up at any time. George may hop on stage with Missy carrying an accordion. This is why you peel those legs away from the leather. Is that Mark Usher?

Near the end of the song here, Josh plays percussion and that's what sets Hutch off into the last solo - the absolute burner. When your friends told you they saw this show and it was crazy and you should have been there and you were mildly upset you missed it? They were probably talking about this song.

Lest we forget Doug Weston!

For the work-to-the-bone grinders who sprint through the beach months in front of flat tops and under heat lamps, traipsing up and down Speedway 6 from the Monument to the Bridges - and especially the ones crossing 137 and 124 on this Monday night in July, getting an electric Keb cameo at an acoustic Josh show is always going to be an occasion to mention. More times than not, it'll unfold into an event. So Lennon & Nilsson, maybe. Taylor & Ronstadt & Browne ... just maybe. There's a lot of talent on this arm out here and when it concentrates in one place, these things can happen - bippity boppity boo.

Josh & Keb finish out the second set for the 50 or so suntanned sticky people dazed and entranced by the display of showmanship these two misshapen twins have put upon them. The cool empty couches awaiting their return all forgotten now.

After the show someone was overheard telling Josh on the patio that "this is exactly the reason people go to see live music."

Agreed.

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