Best events in
Upper Sugarloaf Key

Operating on island time, the Florida Keys offer a laid-back calendar of events and things to do in Upper Sugarloaf Key, FL. Life here revolves around waterfront restaurants and community hubs in the Lower Keys, a distinct and more relaxed alternative to the constant energy of nearby Key West. From live music at local pubs to annual costumed festivals, the area provides a unique slice of Keys culture.

Settle into the casual pace of the Lower Keys, where spots like Mangrove Mama's and Boondocks Grille & Draft House feature regular live music.
For a more concentrated burst of activity, head into Key West to catch a show at the Key West Theater or experience the nightlife on Duval Street at iconic bars like Sloppy Joe's.
Experience local traditions at major annual celebrations like Fantasy Fest or the Key Lime Festival, which draw crowds to Key West.

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Nearby cities

Key West

23 miles away

Marathon

24 miles away

Big Pine Key

6 miles away

Duck Key

34 miles away

Key West

23 miles away

Marathon

24 miles away

Big Pine Key

6 miles away

Duck Key

34 miles away

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HBR Book Webinar: Unspeakable

Mon, Nov 23 • 1:00 PM GMT

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The MI5 Archive: Official Secrets

Fri, Nov 27 • 2:00 PM GMT

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How to Choose a (New) Career Fast

Thu, Dec 3 • 1:00 PM GMT

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JOHN LEVIN MEMORIAL CONFERENCE ON ALZHEIMER'S: BRAIN HEALTH REIMAGINED

Fri, Dec 4 • 10:00 AM EST

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Sorted Live: A Food Nightmare Before Christmas

Sat, Dec 5 • 12:00 PM GMT

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HBR Press Webinar: The Scientific Mindset

Tue, Dec 8 • 8:00 AM EST

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PLAYFUL ARCHITECTURE: Drawing in Colour and Monochrome

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The 1911 Triangle Shirtwaist Factory Fire in NY - Film History Livestream

Sat, Mar 13 • 3:00 PM EST

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HBR Book Webinar: Unspeakable

Mon, Nov 23 • 1:00 PM GMT

Check ticket price on event

The MI5 Archive: Official Secrets

Fri, Nov 27 • 2:00 PM GMT

Check ticket price on event

How to Choose a (New) Career Fast

Thu, Dec 3 • 1:00 PM GMT

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JOHN LEVIN MEMORIAL CONFERENCE ON ALZHEIMER'S: BRAIN HEALTH REIMAGINED

Fri, Dec 4 • 10:00 AM EST

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Sorted Live: A Food Nightmare Before Christmas

Sat, Dec 5 • 12:00 PM GMT

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HBR Press Webinar: The Scientific Mindset

Tue, Dec 8 • 8:00 AM EST

Check ticket price on event

PLAYFUL ARCHITECTURE: Drawing in Colour and Monochrome

Check ticket price on event

The 1911 Triangle Shirtwaist Factory Fire in NY - Film History Livestream

Sat, Mar 13 • 3:00 PM EST

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Events near Upper Sugarloaf Key

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Sunday Recognition Brunch - Key West Oyster Fest 2026

Today • 9:00 AM

Half Shell Raw Bar

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Autumn Pairings: An Evening at the Mansion

Wednesday • 6:00 PM

George's | Café • Bar • Spritz

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Agave Tequila Tasting Class

Wed, Dec 2 • 5:30 PM

526 Angela St

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Mangoes Drag Brunch Royale Christmas Show

Sun, Dec 20 • 11:30 AM

Mangoes Restaurant

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Great Gatsby NYE 2026

Thu, Dec 31 • 8:00 PM

First Flight Island Restaurant & Brewery

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Florida Keys Camp Meeting 2027

Fri, Feb 19 • 6:00 PM

Camp Jackson Sawyer - Boy Scout Camp, Overseas Highway, Big Pine Key, FL, USA

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3rd Annual Moose March

Sun, Mar 7 • 2:00 PM

Key West Moose Lodge 1760

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THE PIRATE SESSIONS VI Album Release Show & Party!

Sat, Apr 3 • 6:00 PM

Pier House Resort & Spa

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Sunday Recognition Brunch - Key West Oyster Fest 2026

Today • 9:00 AM

Half Shell Raw Bar

Check ticket price on event

Autumn Pairings: An Evening at the Mansion

Wednesday • 6:00 PM

George's | Café • Bar • Spritz

Check ticket price on event

Agave Tequila Tasting Class

Wed, Dec 2 • 5:30 PM

526 Angela St

Check ticket price on event

Mangoes Drag Brunch Royale Christmas Show

Sun, Dec 20 • 11:30 AM

Mangoes Restaurant

Check ticket price on event

Great Gatsby NYE 2026

Thu, Dec 31 • 8:00 PM

First Flight Island Restaurant & Brewery

Check ticket price on event

Florida Keys Camp Meeting 2027

Fri, Feb 19 • 6:00 PM

Camp Jackson Sawyer - Boy Scout Camp, Overseas Highway, Big Pine Key, FL, USA

Check ticket price on event

3rd Annual Moose March

Sun, Mar 7 • 2:00 PM

Key West Moose Lodge 1760

Check ticket price on event

THE PIRATE SESSIONS VI Album Release Show & Party!

Sat, Apr 3 • 6:00 PM

Pier House Resort & Spa

Check ticket price on event

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Things to do around Upper Sugarloaf Key

Things to do in Key West

Things to do in Marathon

Things to do in Big Pine Key

Things to do in Duck Key

Frequently asked questions about Upper Sugarloaf Key

Where's a good spot for live music events in the Lower Keys?

The Pub at Sugarloaf KOA is a great community hub for performances. This venue regularly hosts local singers and songwriters from across the Florida Keys. For another classic Keys experience with music, check out the long-standing Mangrove Mama's nearby.

What is the nightlife like around Upper Sugarloaf Key?

The local nightlife is relaxed, centered on waterfront bars with music. Venues like South of the Seven at the Sugarloaf Lodge offer a low-key evening. For a more energetic scene, the bars along Duval Street in Key West, like Green Parrot Bar, are a short drive away.

Are there family-friendly activities in the area?

Yes, several venues offer a casual atmosphere suitable for families. Boondocks Grille & Draft House on Ramrod Key combines dining with an on-site miniature golf course. Many outdoor and waterfront restaurants also provide a relaxed setting for all ages to enjoy.

How can I find local art events in the Florida Keys?

The Morada Way Arts & Cultural District in Islamorada hosts a monthly Monthly Art Walk. This recurring event showcases local and national artists, often accompanied by live music and food vendors, offering a great look into the Keys' creative scene.

What are some classic food and drink experiences in the Keys?

The annual Key Lime Festival in Key West is the ultimate culinary event for the region's signature flavor. Beyond that single event, many local spots offer classic Keys dining. For fresh seafood with a view, try the Schooner Wharf Bar in Key West's historic seaport.

Where can I see a comedy show near Upper Sugarloaf Key?

The Key West Theater is the primary local venue for touring comedy acts. Located in the heart of Key West, it's the main stage for professional stand-up shows and other performing arts events in the Lower Keys.

What’s a good date night idea in the Lower Keys?

A great date night combines dinner and live music at a waterfront spot. Places like Mangrove Mama's or South of the Seven provide a quintessential Keys atmosphere. For a more active date, the weekly Music Bingo at the Sugarloaf KOA pub offers a fun, social event.

What kind of free community events happen in the area?

Many community events are free to attend, though food and drink are extra. Exploring the street fairs during Key West's annual Fantasy Fest is a popular free activity. Also, enjoying the live music at venues like Sloppy Joe's often just requires buying a drink.