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Swap Pins & Test Your Disney Knowledge at Anaheim’s Original Rooftop Bar

Disney Trivia Night graphic at The FIFTH rooftop bar in Anaheim featuring sunset views of the Disneyland® Resort skyline.

Looking for a fresh way to channel your Disney fandom without battling the crowds inside the gates? The ultimate midweek escape for park lovers, trivia buffs, and local craft drink fans has arrived above Harbor Boulevard. 


As Anaheim’s original rooftop destination, The FIFTH is thrilled to host Pins & Pints alongside Disney Trivia as the ultimate Disney-related events taking place on the rooftop every month! Set against the backdrop of our expansive 5,000-square-foot open-air terrace, this evening blends the excitement of Disney® pin trading, competitive trivia, and unforgettable dining at Anaheim's best rooftop bar.


The Ultimate Rooftop Experience in Orange County

Forget balancing pin books on park benches or fighting for elbow room. The FIFTH offers a spacious outdoor environment where you can lay out your lanyards, display rare limited editions, and trade in comfort and style before putting your Disney brainpower to work.


Whether you’re a seasoned collector looking for rare pins, a trivia enthusiast ready to claim bragging rights, or just looking to enjoy local brews under the stars, The FIFTH delivers a vibrant community vibe perched high above Harbor Boulevard.


  • Pins & Pints (5:00 PM – 7:00 PM): Swap pins and socialize with fellow collectors during Happy Hour.

  • Disney Trivia (6:30 PM – 8:30 PM): Gather your team and test your knowledge across classic movies, theme park lore, and iconic characters!

  • Scenic Sunsets & Fire Pits: Watch the Southern California sky shift into vibrant golden hour hues while staying cozy beside our ambient open-air fire pits.

  • Disneyland® Fireworks Views: Stick around after trivia wraps up for direct, unobstructed line-of-sight views of the spectacular Disneyland® Park fireworks.


Sunset Vibes, Craft Cocktails & Menu Favorites

Kick off your evening right during our famous Happy Hour (available Tuesday through Saturday from 5 PM to 7 PM). Indulge in premium food and drink specials while trading pins, then keep the sips and bites coming through trivia night:


Signature Cocktails & Sips

  • Attitude Adjustment: Fortaleza blanco tequila, peach schnapps, lemon juice, passion fruit, strawberry, and simple syrup.

  • Fifth's Old Fashioned: Castle & Key bourbon, Angostura bitters, sugar cube, orange, and cherry.

  • Cherry Bomb: Castle & Key gin, Luxardo Sangue Morlacco cherry, Peychaud’s bitters, Sprite, and lime juice, with simple syrup

  • Sangria at The FIFTH: Christian Brothers brandy, Line 39 cabernet, peach schnapps, triple sec, orange & lime juice, and Opera Prima brut.


Chef-Curated Bites & Entrées

  • Chicken BLT: Grilled chicken breast, bacon, pepper jack cheese, lettuce, tomatoes, bacon aioli on a ciabatta roll, served with garlic steak potatoes

  • Ahi Poke Tacos: Wonton shells, fresh guacamole, green apple kimchi, Cholula mayo, and sesame seeds.

  • Crafted Burger: Grilled ground beef patty, cheddar cheese, chopped bacon, arugula, onion hay, tomato, pickles, and Thousand Island on a brioche bun with fries.

  • Chorizo Mac N Cheese: Shell pasta, pork chorizo, Ibérico chorizo, cheddar cheese, and bread crumbs.

Hotel Guest Perk: Guests staying at Grand Legacy At The Park receive an exclusive 15% discount on food and non-alcoholic beverages at The FIFTH by simply presenting your room key!



Know Before You Go: Event & Venue FAQ

1. What are the event times for Pins & Pints and Disney Trivia?

Pins & Pints takes place during Happy Hour from 5:00 PM to 7:00 PM, while Disney Trivia runs from 6:30 PM to 8:30 PM on the third Wednesday of every month (subject to private event calendar and scheduling updates).


2. Do I need a reservation for Trivia or Pin Trading?

While walk-ins are welcome based on availability, reservations are strongly recommended to guarantee your table for trivia teams and post-event fireworks viewing.


3. Is there a food and beverage minimum?

Yes, The FIFTH maintains a standard $35-per-person food and beverage minimum for all rooftop table reservations.


4. What is the cancellation policy?

Reservations must be canceled at least 24 hours in advance to avoid a per-guest late cancellation fee.


5. Are kids and families allowed?

Yes! All ages are welcome during early evening hours, making trivia and pin trading great for families. Please note that The FIFTH strictly transitions to a 21+ venue after 10:00 PM on the weekends.


Enjoy Your Evening at one of Orange County’s Best Rooftop Restaurants & Bars

Whether you are an Orange County local searching for the best rooftop bar in Anaheim or a visiting guest staying right across from the park, The FIFTH promises an unforgettable evening of pins, craft pints, trivia fun, and panoramic skyline views.


Ready to trade pins, win trivia, and take in the fireworks?


Book Your Table on Our Reservations Page


Don't forget to follow us on Instagram @TheFifthRooftop to stay updated on event schedules, secret drink releases, and monthly trivia themes!


Related Rooftop Experiences & Links

Explore Our Full Food & Craft Cocktail Menu

Learn More About Private Events & Buyouts at The FIFTH

Hotel Accommodations & Perks at Grand Legacy At The Park

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