Labor Day Weekend Activities Around Anna Maria Island

| August 22, 2022

If you find yourself staying in one of our island rental homes around Labor Day, you are in luck. There are a number of activities on and off Anna Maria Island that range from family fun to some party time in the evening.

The Annual Pioneer Days Festival and Parade

The nearby town of Englewood hosts an annual festival that has become a local tradition. The Pioneer Days events take place over a two-week period and include things like a car show, a shipwreck-themed dance and even cardboard boat races. On September 3 and 4, music, food and a beer garden will keep the adults busy while a kids’ play area is there to help your kids burn off some energy. On Labor Day, there is a parade that starts at 9:00 am. The festival is held at Pioneer Park from 8:00 am to 3:00 pm. Parking is at 101 S Orange Ave, Englewood, FL 34223. The parade will be on Dearborn Street in Englewood. Check out their website for a schedule of events.

Ringling Underground

Technically the Labor Day weekend won’t have started on Thursday, September 1, but that doesn’t mean you can’t start celebrating. The nearby Ringling Museum of Art will be hosting the Ringling Underground event. This monthly event features an eclectic mix of local and regional live music. The event is hosted in the museum’s beautiful courtyard and is scheduled to run from 8:00 pm to 11:00 pm. The event is located at 5401 Bay Shore Road, Sarasota, FL 34243. Visit their website to learn more.

Downtown Venice Labor Day Weekend Craft Festival

This is the 13th year for the Venice Labor Day Weekend Craft Festival. Scheduled from 10:00 am to 4:00 pm on September 3 and 4, this festival is free to attend. Discover local artists along West Miami Ave or visit the locally owned shops and restaurants. The historic charm of downtown Venice makes it a fun place to walk. Check the festival website for more information.

NBP Rec Days

Practice rowing where Olympians train. Nathan Benderson Park will host a Rec Day during Labor Day weekend. This unique, man-made water sports facility often hosts competitive events on both the national and international levels. It is considered one of the nation’s premier rowing facilities. On September 3, you can stand-up paddleboarding, kayaking, and canoeing on the lakes of the park. Check out their site for more details.

Ringling Museum

Monday is more than just Labor Day. Mondays are also free admission to the Ringling Museum of Art. This is the official art museum of the State of Florida and houses an impressive collection in its 21 galleries. With more than 10,000 objects that include a variety of paintings, sculptures, drawings, prints, photographs, and decorative arts from ancient through contemporary periods, you are sure to find something you love. The museum is open from 10:00 am to 5:00 pm and is located at 5401 Bay Shore Road, Sarasota, FL 34243.

Of course, you can skip all of that and just relax on the beach or at your luxury vacation rental. Whatever you choose, the Serendipity staff hopes you have a relaxing and enjoyable Labor Day weekend. Contact us at Serendipity and our local experts can help make your visit to our island a memorable one.

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