The calendar has been building toward this all month, and now it is here: Halloween weekend lands on the Gulf Coast in full. The 38th Downtown Venice Art Festival takes over West Venice Avenue, Fright Night dresses up St. Armands Circle and the Sarasota Opera opens its fall season, with a few quieter weeknight treats before the rush. Here is how the week of October 26 through November 1 shakes out.
Thursday: Ghostbusters at the Van Wezel
The week eases in with Ghostbusters in Concert at the Van Wezel Performing Arts Hall on Thursday, October 29, at 7 p.m. The classic film screens with a live orchestra playing the score, a fun midweek pre-Halloween date night before the big weekend. These movie-and-orchestra nights go quickly once word gets around, so grab tickets early. The Van Wezel sits at 777 North Tamiami Trail, right across from the bayfront.
Friday: The Opera Season Opens
Friday, October 30, is a proper downtown occasion: the Sarasota Opera raises the curtain on its 2026-27 fall season at the historic opera house on North Pineapple Avenue. I always tell newcomers this is the night to dress up a little, eat early on the bayfront and let the evening run long. If live music is more your speed, KISS America plays a Halloween benefit at Encore Live at 8341 Lockwood Ridge Road the same night, and Sarasota Fright Fest opens its second run at the fairgrounds from October 29 through 31 for anyone who wants one more scare before the 31st.
Saturday, October 31: Art, Treats & the Circle
Halloween itself is a full day. It starts the way every good Gulf Coast Saturday does, with the Venice Farmers Market at City Hall on West Venice Avenue from 8 a.m. to 1 p.m., then rolls into the 38th Annual Downtown Venice Art Festival, where juried artists line West Venice Avenue from 10 a.m. to 6 p.m. As the afternoon builds, the Downtown Halloween Strut brings trick-or-treating to participating shops along Tampa, Venice and Miami Avenues from 4 to 5:30 p.m., with a Trunk-or-Treat and DJ at the Merchants of Venice lot.
Cross the bay for the evening and Fright Night on St. Armands Circle begins around 5:30 p.m., with the whole shopping district decorated, costumed characters on the sidewalks and candy along the boutiques in the event's 18th year. Dinner on the Circle, then Golden Girls: The Laughs Continue takes the Van Wezel stage for the 7:30 show, a reliably funny cap to a big day. The patio picks in my dining guide are perfect if you would rather stay closer to home.
Sunday: A Second Day of Art & the Drum Circle
Sunday, November 1, brings the art festival's second day on West Venice Avenue from 10 a.m. to 5 p.m., with the sidewalk cafes open for a long lunch between laps. Then close the weekend the way locals do: the Siesta Key Drum Circle gathers on the sand at Siesta Beach about an hour before sunset, free and open to everyone, as the sky goes gold over the Gulf. November's calendar is already filling behind it, from the Sarasota Medieval Fair on November 7 to the Siesta Key Crystal Classic sand sculptors November 13 through 16, and the full season lives in my Community Events guide.
Halloween weekend is also a wonderful time to see Venice and the islands at their liveliest, with the season's first crowds arriving. If you are thinking about making the move, reach out and I will build a tour day around everything you loved this weekend.