Sarasota Weekend Events: November 14–15, 2026
Darren Dowling
Darren Dowling
Looking for interesting things to do in Sarasota this weekend? November 14–15, 2026, brings a variety of events throughout Sarasota and nearby communities, offering something for families, food lovers, music enthusiasts, and anyone interested in exploring the area's culture and lifestyle.
From stepping into a medieval village to discovering local food vendors, enjoying a live concert, or exploring Sarasota's architectural heritage, this weekend offers plenty of opportunities to experience the community.
Whether you're a longtime local, visiting the area, or considering a move to Sarasota or Lakewood Ranch, here are six events worth checking out.
Dates: Saturday and Sunday, November 14–15, 2026
Location: Woods of Mallaranny, Myakka City, Florida
Travel back in time at the Sarasota Medieval Fair, one of the area's most distinctive seasonal attractions.
The fair transforms its grounds into a medieval-inspired village filled with historical characters, themed entertainment, artisan vendors, and food. Visitors can watch knights compete in exciting jousting demonstrations, enjoy live performances, browse handcrafted merchandise, and explore the many attractions throughout the festival grounds.
It's a particularly appealing outing for families, history enthusiasts, and anyone looking for something different from the usual weekend activities.
With its costumes, performances, and lively atmosphere, the Medieval Fair offers plenty of memorable photo opportunities and an entertaining way to spend a day outdoors.
More information: Sarasota Medieval Fair Official Website
Date: Saturday, November 14, 2026
Location: The Mall at University Town Center, Sarasota
Food lovers have a reason to head to University Town Center for the Suncoast Largest Food Truck Festival 10.
The event brings together food trucks offering a variety of dishes, snacks, desserts, and other treats. Visitors can explore different food options, discover local vendors, and enjoy a lively outdoor festival atmosphere.
Whether you're craving savory comfort food, something sweet, or a new dish to try, food truck festivals offer an opportunity to sample different flavors without visiting multiple restaurants.
It's also a great way to support local food businesses and enjoy a casual Saturday outing with friends or family.
Check the event listing for updated hours, participating vendors, and any admission information before attending.
More information: Visit Sarasota County Events Calendar
Date: Saturday, November 14, 2026
Time: 7 PM
Location: Van Wezel Performing Arts Hall, Sarasota
For an evening of live music and exceptional performances, David Foster and Katharine McPhee are bringing their concert experience to Sarasota.
David Foster is an internationally recognized musician, songwriter, and producer with an impressive collection of Grammy Awards and a career spanning decades. Katharine McPhee is known for her powerful vocals, television performances, and Broadway appearances.
Together, they bring a combination of musical talent, storytelling, and familiar songs to the stage.
The performance offers a memorable night out for couples, music enthusiasts, and anyone who appreciates live entertainment.
Tickets are required, and availability may vary. Check the venue's official website for current ticket information.
More information: Van Wezel Performing Arts Hall
Date: Saturday, November 14, 2026
Location: Wellen Park, Venice area
Enjoy a relaxed Saturday outing at the Wellen Park Wine Festival.
Wine-focused community events offer an opportunity to discover different selections, enjoy the surrounding atmosphere, and spend time with friends while exploring one of the region's growing lifestyle destinations.
Wellen Park has become known for its walkable town center, restaurants, community gatherings, and outdoor spaces. An event like this provides another reason to visit and experience the area's social atmosphere.
For adults looking for a more relaxed weekend activity, the wine festival is a nice addition to the calendar.
Be sure to check the official event information for admission requirements, tasting details, hours, and age restrictions before attending.
More information: Wellen Park Official Website
Dates: Saturday and Sunday, November 14–15, 2026
Location: Various locations throughout Sarasota
Sarasota has a distinctive architectural identity, and MOD Weekend offers an opportunity to explore the area's modern design heritage.
Organized by Architecture Sarasota, the event celebrates modern architecture, design, and the buildings and ideas that have helped shape the region's identity.
Visitors interested in architecture and design can discover the influence of Sarasota's modernist movement and learn more about the area's architectural history.
This event is especially interesting for homeowners, design enthusiasts, real estate professionals, and anyone curious about how architecture influences the character of a community.
Sarasota's architectural heritage is also part of what makes the region distinctive. From mid-century modern homes to thoughtfully designed contemporary residences, the area's built environment adds another dimension to its appeal.
Check the organizer's website for the complete program, participating locations, and any registration or ticket requirements.
More information: Architecture Sarasota
Date: Sunday, November 15, 2026
Time: 4 PM
Location: Holley Hall, Sarasota
Wrap up the weekend with an afternoon of music at Sarasota Orchestra's In the Mix performance.
Chamber music offers a more intimate concert experience, allowing audiences to appreciate the individual instruments and musicians while enjoying the interaction between performers.
The program provides an opportunity to experience classical music in a smaller performance setting and discover different musical arrangements.
Whether you're a longtime classical music enthusiast or simply interested in trying something new, this Sunday afternoon performance offers a pleasant cultural outing.
Tickets and program details are available through the orchestra's official website.
More information: Sarasota Orchestra
From the medieval attractions of Myakka City to the food and entertainment around Sarasota and the lifestyle destinations of Wellen Park, the weekend of November 14–15 offers a variety of ways to explore the region.
Here are a few ideas to help plan your weekend:
Remember to check the official event pages for updated schedules, ticket availability, admission requirements, and other important details before heading out.
One of the many advantages of living in the Sarasota region is having access to a variety of experiences throughout the year.
From arts and cultural attractions to food festivals, outdoor recreation, live entertainment, and community gatherings, the area offers plenty of ways to enjoy life beyond the home.
Sarasota's coastal atmosphere, historic neighborhoods, and vibrant arts scene appeal to many homebuyers. Meanwhile, Lakewood Ranch offers a different lifestyle with master-planned neighborhoods, parks, shopping, dining, and community amenities.
Choosing the right property is also about finding a location that supports the lifestyle you want.
Darren Dowling and Beyond Realty specialize in Sarasota and Lakewood Ranch residential real estate, including new construction, relocation, and master-planned communities.
Whether you're moving to Florida, searching for a new home, or exploring your next real estate investment, Darren and the Beyond Realty team can help you understand the local market with strategic guidance and a no-pressure approach.
Explore available properties and learn more about the area at BeyondRealtyFL.com.
Beyond Realty
2170 Main Street, Suite 103
Sarasota, FL 34237
941-204-0493
Event dates are based on published event listings available at the time of writing. Some organizers have not published complete schedules or admission details. Please check the official event websites for the latest information before attending.
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