October is shaping up to be a busy one in Bermuda.

Art Month brings plenty of reasons to get creative, the theatre calendar is packed, Oktoberfest returns to Dockyard and, by the end of the month, Hallowe'en takes over with everything from illusion to costumes and an elaborate Venetian dinner.

Whether you want dinner and a show, a night at the theatre or an excuse to dress up, here’s what’s worth putting on the calendar this month.

Oktoberfest 2026

October 2 to 4 | Victualling Yard, Royal Naval Dockyard

Beer, bratwurst and live music return to Dockyard for three nights of Oktoberfest celebrations.

London’s Oompah Brass will headline each evening, but don’t expect a night of traditional German polkas. The five-piece brass band puts its own spin on rock and pop from artists including AC/DC, Queen, Bon Jovi and Taylor Swift.

Food includes warm pretzels, pork schnitzel, bratwurst, smoked chicken, sauerkraut, spaetzle and apple strudel, with beer from Dockyard Brewing Co.

Bars open at 5.30pm with the band starting at 7pm. Seating options range from $35 general admission to reserved tables with dinner and table service.

Sip & Paint in the Caves

October 4, 11, 18 and 25 | Prospero’s Cave, Grotto Bay Beach Resort

One of the more unusual ways to celebrate Bermuda’s fourth annual Art Month takes you underground.

Local artist Carlos Santana Dill leads a series of Sunday Sip & Paint sessions inside Prospero’s Cave at Grotto Bay. Guests are guided step-by-step through creating their own painting while enjoying complimentary wine.

No serious artistic ability required — the experience is as much about spending an evening inside one of Bermuda’s caves as it is about what ends up on the canvas.

Sister Act

October 8 to 17 | Earl Cameron Theatre

The Gilbert & Sullivan Society of Bermuda brings Sister Act to the Earl Cameron Theatre this month.

Based on the 1992 film, the musical follows disco diva Deloris Van Cartier after she witnesses a crime and is hidden in the last place anyone expects to find her: a convent.

What follows is a high-energy mix of comedy, music, dance and sisterhood as Deloris takes on the convent’s struggling choir.

The production features music by Alan Menken and runs from October 8 through 17.

Witch

October 15 to 23 | Daylesford Theatre

Just in time for Hallowe’en, Witch brings something considerably darker to the stage.

Jen Silverman’s play follows a charming devil who arrives in the village of Edmonton offering residents their darkest wishes in exchange for their souls. Elizabeth, already ostracised by the village and labelled a witch, seems like an easy target — until she proves otherwise.

The darkly comic, subversive retelling of a Jacobean drama explores desire, hope and just how much a soul is worth.

Closing night on October 23 is Costume Night, with audience members invited to wear witch-themed or Hallowe'en costumes.

Live-art dinner

October 17 | The Loren

Dinner becomes part of the performance at The Loren’s Art Month event.

The evening begins with cocktails and an exhibition before guests sit down to a four-course dinner with wine pairings. As each course is served, featured artists will create work live in front of the room, giving diners a look at the creative process as it happens.

Participating artists include Alshante Foggo, Shanna Hollis, Nahshon Hollis, Alice Cedenio, Carlos Santana and Jahbarri Wilson.

The menu includes spiced pumpkin soup, chicken ballotine and mini coconut pavlova. Tickets are $225 per person plus gratuity, with the reception beginning at 7pm and dinner at 7.30pm.

Reza: Edge of illusion

October 30, 31 and November 1 | Earl Cameron Theatre, City Hall

Hallowe’en weekend gets a little magical with the return of illusionist Reza.

Fresh from being named the 2026 Merlin Award winner for International Illusionist of the Year, Reza brings Edge of Illusion back to Bermuda for three performances.

The fast-paced production combines large-scale illusions, sleight of hand, comedy and audience participation, with spectators becoming part of the show.

Tickets start at $65.

Venetian Renaissance Dinner

October 31 | The Loren

If your idea of dressing up for Hallowe’en involves considerably more glamour than gore, The Loren is heading to 16th-century Venice.

Its Venetian Renaissance Dinner promises an evening of masks, candlelight, live music and Italian-inspired dining, with guests encouraged to arrive in Renaissance attire. Traditional Venetian masks will be provided.

The four-course menu includes burratina, jumbo prawn pil pil, a choice of roasted veal loin or truffle risotto and Venetian trifle, accompanied by cocktails, wine and live entertainment from the Violin Sisters.

The evening begins at 7pm and costs $245 per person plus 17 per cent gratuity.

Hallowe’en on UberVida

October 31 | #1 Dock, Front Street

For a Hallowe'en that looks more like a party, UberVida is taking the celebrations on to the water.

This year’s theme is scary movies, with guests encouraged to come as killers, final survivors, horror characters, or whatever else they feel like wearing. Costumes are encouraged but not mandatory.

The 18-plus cruise includes music, Hallowe'en surprises and a cash/card bar. Boarding begins at 7.30pm before an 8pm departure, with the party running until 11pm.

Tickets are $32.