Friends and neighbors,

Anyone else feel like there’s suddenly no time? With so many happenings, you’ll have to choose wisely this week. Gulfshore Playhouse and The Naples Players are in full swing, and Artis—Naples is ramping up its fall season, too.

Halloween festivities start rolling in this weekend (with plenty more next week), and if you haven’t grabbed your Naples International Film Festival tickets yet, there’s still time — most showings still have seats available. And mark your calendars: Mercato’s Hallowine returns next Wednesday. 

Speaking of making the most of your week, if you’re looking to get your business seen by locals, we can help — our readers are passionate about everything happening in Naples, and your message could reach 100,000 of them. Shoot us a message!

Check out the full list of happenings below. And if you need a local to put up your guests, call Dana and save on fees.  

Cheers,

If you have a tip or event to share, email me at [email protected] — I’d love to feature your favorite finds!

1.  Sips and Bites Tasting Event
📅 Thursday, October 23 | 4:30 – 7:30 PM
📍28280 Old 41 Rd., Unit 11, Bonita Springs

Grumpy Goat Coffee hosts a free local tasting fest where you can sip artisan coffee, sample local wines, nibble on cookies, chocolates, sourdough, and even grab a beer biscuit for your pup. Meet local makers and mingle for happy hour. Taste Scotty’s Spanakopita or Kristi’s Key Lime Pie cookies, and be sure to pick up your favorite roast from Grumpy Goat. Free to attend. Event Info. 

2.   15th Annual Stone Crab Festival
📅 All Weekend, October 24-26 | 9:00 – 11:00 AM
📍Tin City, 1200 5th Ave S, Naples

Celebrate the start of stone crab season! Kick off Friday with the ceremonial “cracking of the first claw” at 5 PM, then stick around for live music, seafood feasts, and waterfront fun all weekend long. Free to attend. Event info. 

3.  Saturday Downtown

Halloween Spooktacular and Porsche Naples Trunk or Treat
📅 Saturday, October 25 | 3:00 – 5:00 PM
📍Cambier Park & 5th Ave S, Naples

5th Ave South is also hosting a Trunk or Treat from 3:00 PM to 5:00 PM located at Cambier Park and Park Street with live music, games, costume contest and more. Continue the Halloween Spooktacular fun from 5-8 PM with live musical performances up and down the sidewalks of 5th Avenue South.

Fright @ Night: City of Naples Halloween Party
📅 Saturday, October 25 | 6:00 – 8:00 PM
📍Fleischmann Park, 1600 Fleischmann Blvd, Naples

Head to Fleischmann Park on Saturday for family-friendly Halloween festivities. Enjoy food trucks, games, bounce houses, vendors and more! Event info. 

4.  Ada and the Engine @ The Naples Players
📅 October 15 - Nov. 9 | 7:30 PM, Wednesday- Saturday, 2:00 PM Sunday
📍Prince Studio Theater, 701 5th Ave S, Naples

The Naples Players presents the true story of Ada Lovelace, a pioneering mathematician who revolutionized how we use machines and is considered the first computer programmer. Tickets are $55-$57 (discounts for students, educators and military personnel). 

5.  October Wine Dinner @ Angelina’s
📅Tuesday, October 28 | 6:30 PM
📍Angelina’s, 24041 S Tamiami Trl, Bonita Springs

Tired of your usual haunts? Head over to Bonita Springs for Angelina’s first wine dinner of the season. Take a culinary journey through 5 different courses, each paired with exquisite Tenuta di Biserno wines. Expect duck, tomahawk steak, and Florentine dessert perfection. Tickets are $199 + tax and tip. Call (239) 390-3187 for reservations. Read more about their dinners here. 

6.  Montero Plays Rachmaninoff @ Artis—Naples
📅 Thursday, October 30 & Saturday, Nov. 1 | 7:30 - 9:30 PM
📍Artis—Naples, 5833 Pelican Bay Blvd., Naples

Gabriela Montero opens the season’s Masterworks series with Rachmaninoff’s iconic Piano Concerto No. 2.  The program also features Copland’s Fanfare for the Common Man, Jubilation from Heaven Earth Mankind, and Bernstein’s Symphonic Dances from West Side Story. Get there early for the conductor's prelude discussion, a half hour before showtime. Tickets start at $29-$82. $15 Student with ID. 

7.   Naples Yard & Garden Show
📅 Saturday, October 25 & Sunday, October 26 | 9:00 AM - 4:00 PM (3:00 PM Sun) 
📍14700 Immokalee Road, Naples

Here’s your chance to revitalize your garden. Naples’ Yard and Garden show provides inspiration, plant deals and even informative workshops for your yard all weekend long. Tickets are $5, kids free. 

8.  Trick or Treatment @ 4Ever Young 
📅 Friday, October 24 | 6:00 PM - 8:00 PM 
📍4Ever Young, 9100 Strada Pl, Suite 2135, Naples

Don’t be spooked! Don your costumes, grab complimentary food and drink, and chat with the experts at 4Ever Young. Expect prizes and giveaways. Event info and free sign-up. 

Why It Matters

That’s a wrap for this week’s guide. Between first-crack claws, concert halls, and costume chaos, Naples is humming, and I’m glad you’re here for it. If you go to any of these, tag us so we can share the fun, and don’t forget to cast your vote in this week’s quick poll.

Have a can’t-miss event, hidden gem, or local hero we should spotlight next? Send it my way at [email protected] -- I read every note. And if you’re a local business looking to meet 100,000 engaged Naples readers, let’s chat about a feature or sponsorship that actually moves the needle.

See you around town,

Elizabeth Bellotti
Editor-In-Chief
Naples, Florida
The Naples Florida Review

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