Best Bets! 38 Must-Go Orlando Events This Week

Orlando Date Night Guide is a free guide to the best of Orlando! We're supported by our advertisers when they buy digital ads, listings, content, and through affiliate links, so some things you read might be paid for or if you buy something thru a link on our site we might get a commission.
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Orlando Skyline

Bourbon, wine & foodie events, along with comedy, plays & pub crawls await you this week in Orlando.

Best of DTO Photo Contest Exhibition
Now thru October 15
The Gallery at Avalon Island
FREE Admission

Made in Mexico Cocktail Dinner
Tuesday, September 20, 6-9pm
The Osprey Tavern
$85

Dinner with the Brewmaster
Tuesday, September 20, 7-10pm
Outpost Neighborhood Kitchen
Menu prices vary

Bourbon Curious: A Tasting and Talk with Fred Minnick
Wednesday, September 21, 5-6pm
Soco Thornton Park
$60-$100

Drink Around the Hood
Wednesday, September 21, 7-10pm
Santiago’s Bodega Orlando
$15-$20

Tumbleweed Comedy Tour
Wednesday, September 21, 7:30pm
Orlando Improv
FREE Admission

Some Kind of Wonderful
Wednesday, September 21, 11pm
The Swirlery
FREE Admission

Cirque du Soleil presents OVO
September 21-25
Amway Center
$35 and up

Weekly Pop-up Dining Dinner at The District: Leguminati Thursdays
Thursday, September 22, 6-9pm
The District at Mills 50
FREE Admission (Menu prices vary)

Taste of Downtown Orlando
Thursday, September 22, 6-9pm
Orlando City Hall & City Commons Plaza
FREE Admission (Food sampling tickets available)

First Day of Fall Pub Crawl
Thursday, September 22, 6-11pm
Mills 50 District
$5 Wristband and you can enjoy drink specials at many locations!

California Crush Wine Dinner w/Uncommon Catering
Thursday, September 22, 6:30-9:30pm
Swirlery Wine Bar
$60

Drip’s Local Art Night
Thursday, September 22, 7-10pm
Drip
$5

Pepe’s Truth or Dare Improv at SAK Comedy Lab
Thursday, September 22, 10:15-11pm
SAK Comedy Lab
$6

Food Truck Friday
Friday, September 23, 5-9pm
Artegon Marketplace
FREE Admission (Menu prices vary)

Barks and Crafts Night
Friday, September 23, 6-8pm
Eola Pets
$10-$15

The Bourbon Heritage Dinner
Friday, September 23, 6:30-9:30pm
Lake Eola/Thornton Park; Collette’s Clean Eats
$75

Wine Riffs featuring the Bordeaux Region
Friday, September 23, 7-10pm
Hard Rock Hotel, Orlando
$125

Gezellig Cookies Stroopwafel Baking Demo
September 24 & 25
Williams-Sonoma Park Ave (Sept 24); Williams-Sonoma The Mall at Millenia (Sept 25)
Free

Theatre Minus One presents BLIND LOVE
September 24 & 25
The Abbey
$20, VIP Tables for 4, $125.

Smithsonian Museum Day Live!
Saturday, September 24, All day!
Participating museums & cultural institutions.
FREE Admission

Food Truck Saturday
Saturday, September 24, 12pm-11:55pm
Dead Lizard Brewing Company
FREE Admission (Menu prices vary)

Florida Fanfest on Church Street
Saturday, September 24, 4-8pm
Church Street District
FREE Admission

Orlando Pride vs. FC Kansas City
Saturday, September 24, 5pm
Camping World Stadium
$19 and up

Lake Nona Nights: Crescent Cinema featuring The Indian in the Cupboard
Saturday, September 24, 7:30pm
Crescent Park in Laureate Park
FREE Admission

An Evening with Peter Cetera
Saturday, September 24, 8-10pm
Dr. Phillips for the Performing Arts
$48.75 and up

Sunday Funday Brunch
Sunday, September 25, 10am-2:30pm
Second Harvest Food Bank of Central Florida
$39.95 (Add the Bloody Mary Bar for only $10 more!)

International Food & Drink Festival 2016
Sunday, September 25, 11am-7pm
I-Drive 360
FREE Admission

Milk District Market – September!
Sunday, September 25, 1-5pm
Milk District Market
FREE Admission

Forkplay: Live & Let Dine
Sunday, September 25, 6-9pm
The Whiskey
$75

Orlando Cringe at SAK Comedy Lab
Sunday, September 25, 7-8:30pm
SAK Comedy Lab
$14

Continuing…

A Midsummer Night’s Dream
Now thru September 24 (Select Dates)
Stonewall Bar Orlando
$22

Visit Orlando’s Magical Dining Month
Now thru October 2
Various participating restaurants
Various menu prices

West Side Story
Now thru September 21
Orlando Shakes
$18 and up

Jekyll & Hyde, The Musical
Now thru September 25 (Select dates)
Greater Orlando Actors Theatre
$25

Epcot International Food & Wine Festival
Now thru November 14
Epcot
$97 and up (Valid park admission required)

Universal Orlando Halloween Horror Nights
Now thru October 31
Universal Orlando Resort
$55.99 and up

Food & Wine Weekends
Now thru November 13
Waldorf Astoria Orlando & Hilton Orlando Bonnet Creek
FREE Admission (Menu prices vary)

Global Peace Film Festival
Now thru September 25
Enzian Theater & other locations
$12 and up

A look ahead…

9/30: Jake’s Beer Festival

10/1: Artlando

10/4-10/9: The Illusionists – Live From Broadway

10/6: Whiskey Under Glass

10/9: Feria de Tapa Toro

10/15: Jack in the Park

10/15: Riesling Rendezvous

10/21: PechaKucha Night Orlando v19

10/22: Dance, Dream & Inspire

10/23: Coppertail Brewery Beer Dinner


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