Dunedin Wine and Art Walk: Celebrate the second Friday of the month as downtown Dunedin merchants offer specials and discounts; browse the art exhibits, sip wine at tastings, and enjoy food samplings, entertainment and a drawing. 5:30-8:30 p.m. $10. Pioneer Park, Main Street and Douglas Avenue. (727) 647-8181.
The Odd Couple: Neil Simon's comedy features two friends sharing an apartment whose ideas of housekeeping and lifestyles are as different as night and day. 8 p.m. $8-$25. Tarpon Springs Cultural Center, 101 S Pinellas Ave. (727) 942-5605.
Motorcycle Poker Run Fundraiser: You don't need a motorcycle to participate in Paws For Friendship's second annual ride; you can drive, skate, walk, rollerblade — whatever you choose. 9 a.m.-5 p.m. $20. Quaker Steak and Lube, 10400 49th St. N, Pinellas Park. (727) 572-9464.
Community Cooking: Area cooks teach Jamaican and Cuban cuisine, rooted in African traditions, with a meal after the class. Registration required. Noon-2 p.m. $20. Safford House Historic Museum, 23 Parkin Court, Tarpon Springs. (727) 942-5605.
Chili Cook-Off and Open House: Check out the family-friendly activities at the fire station, including Jaws of Life and canine unit demonstrations, station tours, engine rides and more. Benefits the Children's Burn Foundation of Florida. 1-4 p.m. Free. Largo Fire Rescue Station 41, 180 Fourth St. SW. (727) 587-6737.
Seminole Sound Spectacular: About 22 area and out-of-state marching bands show off their field show performances. The University of Central Florida Marching Knights perform in exhibition only. 2:30 p.m. $15, $10 ages 5-12; 4 and younger free. Seminole High School, 8401 131st St. (727) 501-3439.
Rocktoberfest: Palm Harbor merchants celebrate Oktoberfest with music by the Michael Allman Band (son of Greg Allman), Hope Darling and Radio Crime, along with food, beer, wine and vendors. 5-11 p.m. Free. Historic Downtown Palm Harbor, along Florida Avenue. (727) 224-1359.
Stars and Stripes USO Show: Dance the night away to the Lorri Hafer Swingin' Band at this party with special guest impersonators, paparazzi, a red carpet welcome and show hostesses. Upgrade to VIP and start at 6 p.m. with a full dinner buffet. 7 p.m. $24, $50 VIP. Armed Forces History Museum, 2050 34th Way N, Largo. (727) 539-8371.
Richard Marx: Fresh off releasing Beautiful Goodbye, his first studio album in 10 years, the Grammy award-winning pop/rock singer-songwriter will hit the road for a fall tour. 8 p.m. $44.50-$59.50, $184.50 meet and greet. Capitol Theatre, 405 Cleveland St., Clearwater. (727) 791-7400.
Pretty in Pink: Formerly the Ace of Hearts, this 5K or 15K chip-timed race celebrates the color pink during Breast Cancer Awareness Month. 7:15 a.m. $20 5K, $30 15K. Del Oro Park, 401 McMullen Booth Road, Clearwater. (727) 799-1227.
Herencia Hispana: Latin station Maxima 92.5 is hosting this concert featuring internationally known performers from Puerto Rico, the Dominican Republic and Columbia. Noon. $20; $75 VIP; free children younger than 10. Coachman Park, 301 Drew St., Clearwater. (727) 563-8837.
Sukkot Festival of the Harvest: To celebrate this holiday of giving thanks for the bounty of the earth, guests will sample vegetarian foods, sit in a Sukkah and enjoy '60s music by Mary & the MDs. 6 p.m. $10, $5 children. Temple B'nai Israel, 1685 S Belcher Road, Clearwater. (727) 531-5829.
Florida Orchestra Masterworks: Beethoven and Rachmaninoff: Under the direction of guest conductor Joshua Weilerstein, the orchestra presents John Adams' Lollapalooza, Beethoven's Piano Concerto No. 1 and Rachmaninoff's Symphonic Dances, Op. 45. 7:30 p.m. $15-$45. Ruth Eckerd Hall, 1111 N McMullen-Booth Road, Clearwater. (727) 791-7400.
Hope Floats on Bra Day: The event under the stars includes appetizers, a "Wish Boat" and cash bar. Benefits My Hope Chests' reconstruction education programs and surgeries. 5:30-8:30 p.m. $50. Hyatt Regency Clearwater Beach Resort & Spa, 301 S Gulfview Blvd. (727) 488-0320.
Clearwater Jazz Holiday: The 35th annual four-day event features a variety of jazz artists performing at a waterfront setting. 4 p.m. $15-$150, 12 and younger free. Coachman Park, 301 Drew St. (727) 461-5200.
Oktoberfest and Family Fall Festival: Midway rides, games, food, an oversized flea market, an Oktoberfest tent (6-10 p.m. Thursday) and entertainment. 5-9 p.m. Free. Our Lady of Lourdes Catholic School, 750 San Salvador Drive, Dunedin. (727) 733-3776.
Making Waves Educational Series: Heather Masonjones, a biology professor at the University of Tampa, will discuss the unique behaviors and reproductive physiology of seahorses. 6-8 p.m. Free. Clearwater Marine Aquarium, 249 Windward Passage. (727) 441-1790.