There is something about October that invites adventure! Not sure you can exactly put a finger on it, maybe it's childhood, mischief, merriment, expectation, or the decadence of the month, who knows. What we do know is even though it is a warm month for us, with little change in the weather, we too enjoy Oktoberfesting and gearing up for Halloween! This weeks Top 10 Things to Do This Weekend in Tampa Bay includes naughty choices including lots of 'boos' and several family-friendly and foodie events too. So let's celebrate the season, and get out this weekend, it' time to play like a barrel of monkeys!  NOTE: Find links to Oktoberfest and Halloween events in Hillsborough and Pinellas at the end of this article.

Top 10 Things to Do This Weekend in Tampa Bay, Friday

6th Annual Clearwater Beach Chalk Art Festival  Begins 9 am Friday, Ends Sunday

The Clearwater Beach Chalk Art Festival is once again hosted by the local Chamber is fun and FREE!  For three days, 40 plus talented chalk artists will transform the sidewalks of South Clearwater Beach into creative larger-than-life-canvases, allowing the public to get a rare glimpse into the way art is made. And you get to choose a favorite artist by voting for the "People's Choice Award." One of our family-friendly things to do in Tampa Bay the festival includes a kid's zone, arts and crafts vendors, live music at this open-air gallery on one of Americas Best Beaches!

333 S. Gulf Blvd., Clearwater Beach FL, 33767. Phone (727) 447-7600

33rd Annual Frenchy's Stone Crab Weekend 12 pm

An annual favorite on Clearwater Beach it's time once again for this, Frenchy's 33rd Annual Stone Crab Weekend.  Featuring fresh-off-the-boat stone crab claws supplied by Frenchy's Stone Crab Company at deeply discounted prices this party starts on Friday at noon and runs through Saturday at 10 pm. Admission is free, food and drinks are extra, noon to 10 pm both days, head to Frenchy's Cafe for live music, raffles, drink specials and the best seafood fest of the year! Click the link above to navigate to their website for additional information.


466 Causeway Blvd, Dunedin FL, 34698. Phone (727) 286-6139

Top of the Bay Oktoberfest 2017 Begins 5 pm Friday, Ends Sunday at 6 pm

Roll Out The Barrels...Oktoberfest is here! Head to the top of the bay area for a great time with your family and friends as they tap the keg at Tampa Bay Downs! Parking is FREE as the Upper Tampa Bay Chamber of Commerce welcomes you to this three-day fest designed to bring the best of Old Bavaria and new Florida together for authentic German food, drink, music, and dancing. This is so authentic we call it Florvaria! This family-friendly event in Tampa offers a carnival and midway, an arts and crafts show and loads of interesting vendors.

Insane Clown Halloween Party 9 pm

Celebrate Halloween a little early with the INSANE Clown party at Club Prana featuring 5 Levels of Scary and Creepy clowns! Do you dare?

Top 10 Things to Do This Weekend in Tampa Bay, Saturday

Tampa Bay Wing Fling 11 am to 10 pm

The Inaugural Tampa Bay Wing Fling, Tampa's biggest Wing Festival and Competition kicks off at 11 am in  Curtis Hixon Waterfront Park this Saturday. NOTE: Pets are NOT allowed at this event.  VOTE for the best Wings as you experience more than a dozen local wings spots dishing up their best while you enjoy live music, cold beer, signature bourbon drinks, and fun, interactive games like a Chicken Toss Contest, Costume Contest, a Chicken Run, and much more!  GA Tickets start at only $15. Children 12 and under are FREE.

Related Content: Get Fired Up for the Inaugural Tampa Bay Wing Fling

600 N. Ashley Drive, Tampa FL, 33602.

Ybor Oktoberfest Pub Crawl 2017 2 pm to 6 pm

Time to break out those dirndls and lederhosen and join the Ybor City Chamber of Commerce for their 8th Annual Oktoberfest Pub Crawl through Ybor City.  Experience ten bars and enjoy pretzels, brats, stein hoisting, beer boots and costume contests! Your ticket includes a free das boot with lanyard, 4oz pour of Oktoberfest beer at each location, food and drink specials. General Admission $25 (Sept 1- Oct 20th) / Day of Event $35

1800 East 9th Avenue, Tampa FL, 33605. Phone 813-241-8838

Dunedin Craft Beer & Crab Festival Begins 2 pm Saturday, ends 8 pm Sunday

Dunedin's Craft Beer & Crab Festival Food brings vendors, arts and craft artisans, civic groups, musicians and more to this quaint waterfront city once again. In their 7th year, the party begins Saturday in Edgewater Park at the Dunedin Marina and ends Sunday night. This is a family-friendly event and pet-friendly too! Admission is FREE, food and drinks are extra.  Enjoy local favorites; lobster rolls, fried shrimp, grouper, fish tacos, bbq, snow cones, burrito bowls, chowders, pizza, organic and veggie dishes, and of course…CRAB along with craft beer from a town that makes enjoying craft beer a true art. Scheduled to appear are: The Black Honkeys, She’s That Dude, Jeriko Turnpike, The Outpatients and more. 

51 Main St, Dunedin FL, 34698. Phone (727) 733-2542

6th Annual Pub CrawlOWeen 6 pm to 11:30 pm

Club Sport's 6th Annual "Pub-Crawl-O-Ween" Costumed Pub Crawl is back in Downtown St. Pete Saturday. Head out to 5 different bars for a FREE drink at each while decked out in your Halloween best!  Bars included are Caddy's on Central, Yard of Ale St Pete, MacDinton's St Pete, Ringside Cafe, and The One Night Stand

Downtown, Saint Petersburg, Saint Petersburg FL, 33713.
Top 10 Things to Do This Weekend in Tampa Bay, Sunday

Fox Squirrel Corn Maze 2017 Sunday

Enjoy this Sunday Funday with a Corn Maze, Pumpkins, Hayrides, Games, Arts and Craft vendors and much, much more! Get out into the country and visit a farm this year. #SupportLocalFarming

Related Content:  Best Pumpkin Patches, Fall Festivals, Hay Rides and Corn Mazes in Tampa Bay for The Kid in All of Us

3002 Charlie Taylor Rd, Plant City FL, 33565. Phone (813) 756-8918

A Night at the Museum 2 pm to 6 pm

As the Tampa Bay History Center closes the exhibits come alive this Sunday afternoon from 2 pm to 6 pm. Catch pirates, explorers, Florida pioneers, and more interesting characters sneaking around the galleries during A Night at the Museum.

801 Old Water St, Tampa FL, 33602. Phone 813-228-0097
October is full of fun things to do, favorite annual events and more.  be sure to visit these pages for details on events not mentioned in Top 10 Things to Do This Weekend in Tampa Bay:. Oktoberfest in Pinellas and Oktoberfest in Tampa ~ Halloween in Pinellas and Halloween in Tampa. And visit our Fall in Tampa page too! Register on 813area and 727area to stay connected to fun things to do in Tampa Bay, get restaurant recommendations, stay on top of local Sports in Tampa and much more. Your subscription is free.