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Sunday, May 3 -
Sunday, May 31
10:00am - 1:00pm
Jeremy Carter: Jazzy Sunday Brunch!
Your Sunday soundtrack is set. Join us for live jazz and unforgettable brunch favorites at HEW Parlor & Chophouse!
Monday, May 4 -
Monday, May 25
6:00pm - 9:00pm
Peggy Morris: Live at Fenway on Monday nights!
Join us in the heart of Fenway on Monday evenings for live jazz, soulful energy, and a captivating performance by Peggy Morris.
Tuesday, May 5 -
Tuesday, May 26
6:00pm - 9:00pm
Kyle Schroeder: Live at Fenway on Tuesday nights!
Let the night unfold in rhythm as Kyle Schroeder brings vibrant jazz energy to the Fenway lobby stage every Tuesday night!
Sunday, May 17
10:00am - 1:00pm
Mutts & Mimosas: Adoption Event at Fenway!
$0
Join us on Fenway Hotel’s lawn for pups, mimosas, and community fun at Mutts & Mimosas!
Monday, May 18
6:30pm - 8:30pm
Room 27 Speakeasy Cocktail Experience: 05.18.26 – 6:30 PM
$10
Step behind the hidden door and toast to secrets worth savoring with a speakeasy cocktail experience in Room 27.
Monday, May 18
9:00pm - 11:00pm
Room 27 Speakeasy Cocktail Experience: 05.18.26 – 9:00 PM
$10
Step behind the hidden door and toast to secrets worth savoring with a speakeasy cocktail experience in Room 27.
Tuesday, May 19
7:30pm - 9:30pm
Paint the Sunset at Fenway! 05.19.26
$45
Fenway Hotel sets the tone for a relaxed, sunset-inspired paint night with Bree Carns of Let’s Paint & Party!
Saturday, June 6
11:00am - 2:00pm
Pride & Pours: Pool Party at Fenway!
$30
Celebrate Pride with a pool party filled with tastings, giveaways, and a meaningful cause at Fenway!
Sunday, June 7
1:00pm - 4:00pm
We Inspire 2026 Season Kickoff at Hi-Fi Rooftop Bar!
Give your wardrobe a purpose that goes further at Hi-Fi Rooftop Bar!
Tuesday, June 9
7:00pm - 9:00pm
June Book Club: 06.09.26
$0
Gather with fellow readers this April for Fenway Hotel’s Book Club and a discussion of The Magnificent Lives of Marjorie Post.
Tuesday, July 14
8:00pm - 10:00pm
Paint the Sunset at Fenway! 07.14.26
$45
Create, sip, and unwind as Fenway Hotel hosts a sunset-inspired painting experience with Let’s Paint & Party, led by local artist Bree Carns.
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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!