The last week of October on the beaches is easygoing in the best way. On Friday, October 23, Corey Avenue has live music at Chill Restaurant and Bar while the Treasure Island Recreation Department hosts a family Halloween night a few miles up Gulf Boulevard. The Corey Avenue Sunday Market returns on October 25, and the monthly Sip and Stroll closes the window on Friday, October 30. Between October 22 and October 30, here are four picks that show off the friendliest side of the island.
Chill's Live Music Entertainment on Corey Avenue
Why It Stands Out
Friday, October 23, from six until ten in the evening, Chill Restaurant and Bar at 357 Corey Avenue features the band Motel Funk. Corey Avenue's event calendar describes an evening of live music, food, and cocktails at a neighborhood spot where, in the restaurant's words, the community comes together.
Best For
Couples, friends, and neighbors looking for an easy Friday night close to home. It is a good way to see how lively the avenue gets after dark.
Timing and Planning
No cover or ticket price is listed. For tables or questions, call the restaurant at 727-360-2445. Free parking is available at City Hall and along the 200 and 400 blocks of Corey Avenue.
Halloween Spooktacular in Treasure Island
Why It Stands Out
Friday, October 23, from six until eight in the evening, the City of Treasure Island Recreation Department hosts its Halloween Spooktacular at the Treasure Island Community Center, 1 Park Place. Expect trick or treating, interactive games, bounce houses, and food trucks, with a costume contest at seven.
Best For
Families with young children and anyone who wants to see a small beach town do Halloween the cheerful way. It is a few miles north of Corey Avenue, so it works as an early evening stop.
Insider Tip
The city's announcement lists no admission price or registration. Questions go to the Recreation Department at 727-547-4575, extension 246. Dress for the weather and plan on a little time to find parking.
Corey Avenue Sunday Market
Why It Stands Out
Sunday, October 25, from ten in the morning until two in the afternoon, the Corey Avenue Business District and Florida Penguin Productions host the weekly Sunday Market. Local vendors sell fresh produce, artisanal foods, handmade crafts, specialty products, and gifts, with live music along one of the most walkable streets in the beach towns.
Best For
Everyone. Locals stock up on the week's produce and breakfast, and visitors get an easy introduction to downtown St. Pete Beach.
What to Expect
No price is listed for visitors, and the market runs from October through May on Sundays from ten to two. Bring a tote bag, arrive before noon for the best selection, and plan to linger over coffee.
Corey Ave Sip & Stroll
Why It Stands Out
Friday, October 30, from five until eight in the evening, the Corey Area Business Association hosts its monthly Sip and Stroll on the last Friday of the month. It is a self guided evening through Corey Avenue's independent shops, restaurants, galleries, and wellness businesses, and participating businesses offer drinks, dining, and deals that change from month to month. Admission is free.
Best For
Friends who want a relaxed way to end the week, and new neighbors who want to meet the shop owners and restaurant teams that keep the avenue going.
Timing and Planning
The host's page does not list entertainment for this date, and it points to the Corey Avenue Business Association's Facebook page for the month's specials. Free parking is available at City Hall, 155 Corey Avenue, in the 200 and 400 blocks, and at the St. Pete Beach Public Library.
Event Q&A
Which event is best for families?
The Halloween Spooktacular on Friday evening, with its games, bounce houses, and costume contest. The Sunday Market is also easy with kids in tow.
Which event feels most on-brand for a date night?
Live music at Chill on Friday, October 23, or the Sip and Stroll on Friday, October 30. Both end naturally with dinner on the avenue.
Which event is worth planning ahead for?
The Halloween Spooktacular, mostly for parking and timing, since it runs only two hours. The Sunday Market runs until two, so mornings give the best selection.
Which event gives the best sense of local community?
The Sip and Stroll. It is organized by the neighborhood's own business association, and the shop owners are the ones pouring and chatting.
What is coming right after the window?
The Corey Avenue Sunday Market continues every Sunday through May, and the Sip and Stroll returns on the last Friday of each month.
