Events Calendar

All Events

JAZZ

Sunday, October 5

10am - 2pm

Jazzy Brunch 10.05.25

Sunday Soul Food!

Event Sold Out
tent

Monday, October 6

6:30pm - 8:30pm

Room 27 Speakeasy: The Forgotten Tent 10.06.25 6:30pm

$10

The Hidden Circus!

Only 5 tickets left!
tent

Monday, October 6

9:00pm - 11:00pm

Room 27 Speakeasy: The Forgotten Tent 10.06.25 9:00pm

$10

The Hidden Circus!

pEGGY

Monday, October 6

6:00pm - 9:00pm

Peggy Morris: Live at Fenway! 10.06.25

Jazz it up!

Event Sold Out
tent

Tuesday, October 7

6:30pm - 8:30pm

Room 27 Speakeasy: The Forgotten Tent 10.07.25 6:30pm

$10

The Hidden Circus!

clown

Tuesday, October 7

9:00pm - 11:00pm

Room 27 Speakeasy: The Forgotten Tent 10.07.25 9:00pm

$10

The Hidden Circus!

Kyle-LiveMusic-FenwayHotel-2025

Tuesday, October 7

6:00PM - 9:00PM

Kyle Schroeder: Live at Fenway! 10.07.25

Toe Tapping Jazz!

Event Sold Out
tent

Friday, October 10

6:30pm - 8:30pm

Room 27 Speakeasy: The Forgotten Tent 10.10.25 6:30pm

$20

The Hidden Circus!

Only 1 ticket left!
tent

Friday, October 10

9:00pm - 11:00pm

Room 27 Speakeasy: The Forgotten Tent 10.10.25 9:00pm

$20

The Hidden Circus!

Old Fashioned Week Graphic

Friday, October 10 -

Sunday, October 19

4:00pm - 10:00pm

Sip For a Cause: Old Fashioned Week at Fenway

Every Sip Counts!

jazz

Sunday, October 12

10am - 2pm

Jazzy Brunch 10.12.25

Sunday Soul Food!

peggy

Monday, October 13

6:00pm - 9:00pm

Peggy Morris: Live at Fenway! 10.13.25

Jazz it up!

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Searching for Dunedin events with a different vibe? Inspired by its roots in live radio, Fenway continues to channel the energy of the past and keep the beat alive. Plug in to that enduring vibe with an ever-changing lineup of adventures below. Be sure to check back often as we’re always updating this playlist!