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Cinema at The Bay: Happy Gilmore

The Oval 1055 Blvd of the Arts, Sarasota, Florida

Enjoy a free outdoor movie under the stars at The Bay! In celebration of the opening day of the US Open. (PG-13) – “Happy Gilmore”follows an aspiring ice hockey player (Adam Sandler) who, after failing to make a hockey team due to his aggressive style and lack of skating skills, finds himself in a bind when his grandmother’s house is threatened by the IRS. He then unexpectedly discovers a talent for golf and enters a golf tournament to win the prize money and save his grandmother’s home.

USRowing Youth National Championships

Nathan Benderson Park 5851 Nathan Benderson Circle, Sarasota, FL

Witness the nation’s premier youth rowing athletes compete on one of the finest rowing courses in the world—Nathan Benderson Park in Sarasota. The USRowing Youth National Championships is the final regatta of the youth rowing season and draws more than 2,000 rowers from across the country for three days of elite competition.

Jazz Thursdays at Sarasota Art Museum

Jazz Thursdays at Sarasota Art Museum

Unwind at Jazz Thursdays, a vibrant monthly gathering at the Sarasota Art Museum. Held on the second Thursday of each month, this event brings together live jazz music, inspiring art, and a lively community vibe. Enjoy performances under the stars on the Marcy & Michael Klein Plaza, explore the galleries with extended hours, and grab a bite or a glass of wine at Bistro, which opens at 5:00 PM with a special evening menu. Whether you're a jazz aficionado or just looking for a fun night out, Jazz Thursdays offer a cultural escape like no other in Sarasota.

Free Music Friday Night Concert

Kick off your weekend with great tunes and local vibes at the Free Music Friday Night Concert, a beloved outdoor concert series held in downtown Venice. Each Friday evening, a different local band or solo artist takes the stage to deliver live music spanning genres like rock, jazz, blues, country, and more. Bring a chair or blanket, grab a bite from nearby restaurants, and enjoy a relaxed, family-friendly evening under the stars. With no admission fee and a welcoming community atmosphere, this weekly event is a perfect way to support local talent and unwind at the end of the week. Centennial Park Gazebo200 W Venice Ave, Venice, FL 34285

Free Outdoor Movie – Waterside

Free Outdoor Movie Series – Waterside

Waterside Park 1560 Lakefront Dr, Sarasota, fl

Enjoy a magical evening under the stars at the Free Outdoor Movie Night held monthly at Waterside Park in Lakewood Ranch, Sarasota, FL. Hosted on the second Friday of each month, this family-friendly event invites the community to bring blankets, lawn chairs, and picnic baskets to watch a movie on a giant inflatable screen in a scenic waterfront setting.

Movie in the Park at Waterside Place

Movie in the Park at Waterside Place

Enjoy a family-friendly movie night under the stars. The first 220 attendees will receive a free cookie from Dirty Dough Cookies, courtesy of Grace Community Church. There will also be inflatables for kids and concessions available from We B’ Poppin Popcorn and Kettle Corn. Remember to bring your own blankets or lawn chairs.

Downtown Sarasota Farmers Market

Downtown Sarasota Farmers Market

Downtown Sarasota Farmers Market 1 N Lemon Ave, Sarasota, FL

Enjoy a vibrant and lively market experience every Saturday in the heart of Downtown Sarasota! The Sarasota Farmers Market features over 70 vendors offering fresh produce, artisan foods, local seafood, plants, handmade crafts, and more. Stroll through the market, listen to live music, and discover unique finds while supporting local farmers, bakers, and artists. The market is family-friendly and pet-friendly, making it a perfect Saturday morning tradition for all ages. Come early for the best selection and enjoy the downtown Sarasota atmosphere.

Sarasota Cars & Coffee

Sarasota Cars & Coffee

The Mall at University Town Center 140 University Town Center Drive, Sarasota, FL

Join fellow car enthusiasts at Sarasota Cars & Coffee, a monthly gathering showcasing over 500 vehicles ranging from vintage classics and custom builds to exotic supercars. Enjoy complimentary coffee from Mademoiselle Paris and Chick-fil-A, live music, and a vibrant community atmosphere. The event supports local charities, with different beneficiaries each month. 

Bradenton Public Market

Bradenton Public Market

Old Main Street Downtown Bradenton Old Main Street, Bradenton, FL

Welcome to the Bradenton Public Market, a place where the community meets each week to enjoy fresh produce, local art, music, and free family activities on Old Main Street.Since 1979, the Bradenton Public Market has been a cherished weekly tradition, transforming Old Main Street into a vibrant, open-air marketplace. Each Saturday from October through May, locals and visitors alike gather to explore over 80 vendors offering fresh produce, artisanal goods, local art, and delicious prepared foods. The market also features live music, chef demonstrations, and family-friendly activities, making it a delightful outing for all ages.

32nd Annual Downtown Venice Craft Festival

Downtown Venice Miami Avenue, Venice, FL

Now celebrating its 32nd year, the Downtown Venice Craft Festival returns with a two-day outdoor showcase of creativity, craftsmanship, and community. Stroll along the charming, shaded streets of historic downtown Venice and explore over 100 booths of handcrafted goods made by artisans from across Florida and beyond.

Towles Court Art Studios Open Studio Night

Towles Court Art Studios Open Studio Night

Stroll through one of Sarasota’s most eclectic and charming arts districts during the Artwalk at Towles Court, a vibrant celebration of creativity held on the third Friday of each month. This monthly event invites locals and visitors alike to explore artist studios, galleries, and shops showcasing fine art, sculpture, pottery, jewelry, and more. Live music fills the air as guests enjoy complimentary refreshments and the chance to meet the artists behind the work. Many participating studios offer demonstrations, making it a fun and interactive experience for all ages.