VIP FYI

October in St. Thomas & St. John

Halloween, fall fun and local happenings on island. Your month at a glance. Details can change, so confirm with hosts before you go.

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Two pumpkins resting on a rock above the turquoise water, framed by sea-grape trees in the US Virgin Islands

Pumpkins meet paradise. Fall has landed in the USVI.

Week 1 · Oct 1–6

Thu, Oct 1

FAPA & FBT Fundraiser Dinner

Sambuca's, Frenchtown · 5–9pm

Fri, Oct 2

Taphus First Friday

Taphus Beer House · 5:30pm until late · Benefiting Cancer Support VI

Fri, Oct 2

Free Flow Fridays

CMCArts · 6–8pm · Every First Friday

Sat, Oct 3

Oktoberfest Benefit

My Brother's Workshop Main Campus (behind Home Depot, Estate Donoe) · 12–6pm

Sat, Oct 3

Pets With Wings Block Party

Rock City Tacos and Tillett Gardens · From 5pm

Sat, Oct 3

Trunk or Treat with the Top Notch Band

Mango Tango Art Gallery · 5:30–8:30pm

Sat, Oct 3

Power Shift with Dezarie and Michonde

The Mustard Seed · 7pm–12am · $35 at the door

Tue, Oct 6

Sip & Paint with Katy Turner Art

Island Grind, Main Street · 6–8pm · Book online with Katy Turner Art

Week 2 · Oct 8–11

Thu, Oct 8

Scheme Queens 2: Caribbean Heist Premiere

Caribbean Cinemas, Market Square · Red carpet at 6pm

Thu, Oct 8

Rumporium Rum Class

Lavalette's at Hotel 1829 · 6–7pm

Fri, Oct 9

Birth Papers: A Caribbean Design Show, Closing Celebration

81C, Charlotte Amalie · 6:30pm

Sat, Oct 10

Harvest Festival & Pumpkin Patch

Magens Bay (Fairchild's Beach Bar & Grill) · 12–5pm

Sun, Oct 11

OysterFest on the Harbour

Cuvée, Frenchtown · 4–8pm

Sun, Oct 11

Senatorial Candidate Forum

Franklin A. Powell Sr. Park, St. John · 4pm · Hosted by Alpha Kappa Alpha, Sigma Theta Omega Chapter · Food and drinks on sale

Week 3 · Oct 12–18

Mondays
Oct 12, 19, 26

Theater Makeup Masterclass

St. John School of the Arts · 4:30–6:30pm · $125

Fri, Oct 16

Bubbles & Caviar with Cardow Wine & Spirits

Lavalette's at Hotel 1829

Sat, Oct 17

Paradise Point Road Race

7am · Runners and walkers of all ages · Benefits the Partners for Strings Youth Orchestra · Sign up at paradisepointroadrace.com

Sat, Oct 17

Spookyween Sip & Paint

Don Felito's Cookshop, Charlotte Amalie · 4–8pm · Kids' Halloween painting · Tickets on Eventbrite

Sat, Oct 17

Virgin Islands Noir

Bajo el Sol Gallery, St. John · 5pm

Sat, Oct 17

Pumpkin Paint & Sip

The Roasted Coconut, Bovoni · 6–8pm · Charcuterie and a drink included · Tickets on Eventbrite

Sat, Oct 17

R&B Masquerade Party

Muse USVI · $20 before 11pm · Live DJs · Info: 404-272-8491

Sat, Oct 17

Top Shelf Mixology Masterclass (Day 1)

Cardow Rum Room · $85 ($65 early bird) · Weekend pass $130 ($99 early bird) · Enroll: topshelfmixo@gmail.com or 340-204-1040

Sun, Oct 18

Canvas & Cocktails (Day 2)

Lindbergh Bay Beach Hotel · $65 ($50 early bird) · Enroll: topshelfmixo@gmail.com

Sun, Oct 18

Boozy Brunch: Pick Your Poison

Cové Lounge, Charlotte Amalie · Brunch 10am–3pm, day party 4–8pm · $55 three-course prix fixe with bottomless mimosas · Reservations: 340-209-4316

Week 4 · Oct 24–28

Sat, Oct 24

Montessori Fall Fest & Halloween Movie Night

Montessori School · Fall Fest 3–6pm, then a Halloween movie night at 6pm

Sat, Oct 24

Fright Night

Joseph Sibilly Elementary School · 4–10pm · Haunted house, games and food · Free shuttle · Tickets through Joseph Sibilly School

Sat, Oct 24

Wine Pon Mi: 90's Lime

KAM Experience · 6pm–1am · 21+ · 90s party benefiting ElevateWi · Tickets on Eventbrite

Sat, Oct 24

Socaween 2026: Chapter X

The Terrace at Muse · 9pm–3am · 18+ · Soca, live music and costumes · Tickets on Eventbrite

Sun, Oct 25

Howl-O-Ween Community Trunk or Treat

Humane Society of St. Thomas · 4–7pm · Free · Games, prizes, adoption spotlights, food for sale

Wed, Oct 28

Paint Night with Katy Turner

The Shack at Hull Bay · 6–8pm · Sponsored by Cardow Wine & Spirits · Book online with Katy Turner Art

Halloween Week · Oct 29–31

Oct 29–31

Nightmare Manor

Humane Society of St. Thomas · 6–9pm · $20 adults, $5 kids · Tickets: 340-473-6471

Fri, Oct 30

Downtown Bar Crawl with Costume Contest

Downtown Charlotte Amalie · 6–11pm

Fri, Oct 30

Halloween Costume Party

Jolly Roger's at Blackbeard's Castle · 5pm until · DJ General Kuntry, drink specials, VIP cabanas, free shuttle · Costume contest with an overnight hotel stay for first place

Fri, Oct 30

St. John Trunk or Treat

Cruz Bay gravel lot · 4–7pm

Sat, Oct 31

VIPD Trunk or Treat

Fort Christian parking lot · 12–3pm · Drive-thru · Register a trunk: 340-514-8006

Sat, Oct 31

Kids Halloween Party

Emile Griffith Park · 2–7pm · Costumes, treat bags, food, drinks and music

Sat, Oct 31

Rock City Rollers Halloween Skate Party

Montessori School · 3pm–12am · $10 entry, $5 skate rental · Free candy and costume contest · Info: 410-570-1001

Sat, Oct 31

Dueling Discos

Sibs on the Mountain · Obsession kicks off the night, then Supa Zulu takes over · Disco costume prizes for best dressed

Sat, Oct 31

All Hallows' Eve Champagne Dinner

Lavalette's at Hotel 1829 · Book on Resy

All Month & Weekly

Oct 1–31

Beyond Limits Fitness Grand Opening Special

beyondlimits.fit/saint-thomas

Tuesdays & Fridays

The Shack at Hull Bay

Bingo Tuesdays 5–9pm · Family Movie Night Fridays 6:30pm

Sundays

Bingo at The Windmill Bar

4–6pm

Sundays

Sunday Lacrosse at Antilles Field

Kids play 10–11am, then adults practice alongside the national team 11am–1pm

Through Oct 31

Elementary, Middle School & Girls JV Flag Football

Games every other day at Lionel Roberts Stadium or Antilles Field · Come out and cheer!

Where to Do Yoga

St. Thomas

Ambient Yoga

Yacht Haven Grande · Daily classes for all levels · Schedule and rates at ambientvi.com

St. John

Love City Yoga

Cruz Bay · Schedule and rates at yogastjohn.com

Where to Watch Football

St. Thomas: Dog House Pub · The Island Green · Tap & Still · The Shack at Hull Bay · Sibs on the Mountain · Rum Island Pub

St. John: Upstairs Bar · Greengo's

Details can change, so confirm with hosts before you go. Want your event added, or need a change? Email us.

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