Discovering Delray and Beyond
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September 2026

1. West Palm Beach Home Show – West Palm Beach

Dates: September 11–13
Why it’s special: A large home improvement and design expo featuring remodeling ideas, décor, landscaping, products, demonstrations, and local home professionals.
Learn more:
https://www.southfloridafair.com/events


2. Fall Harvest Craft Fair – West Palm Beach

Dates: September 12–13
Why it’s special: A seasonal craft fair featuring handmade goods, fall décor, gifts, and local vendors—perfect for getting an early start on fall shopping.
Learn more:
https://www.southfloridafair.com/events


3. Mari Froes at The Bandshell – Miami Beach

Date: September 12
Why it’s special: Brazilian singer-songwriter Mari Froes brings her blend of Brazilian popular music, jazz, samba, and contemporary sounds to the Miami Beach Bandshell. The official Miami Beach calendar confirms the September 12 performance.
Learn more:
https://events.miamibeachfl.gov/events/month/2026-09/


4. Ocean Drive Promenade Music Series – Miami Beach

Dates: Sundays throughout September
Why it’s special: Free outdoor concerts near Ocean Drive bring live music and a relaxed Sunday-evening atmosphere to one of Miami Beach’s most famous locations. The series is scheduled for September 13, 20 and 27.
Learn more:
https://events.miamibeachfl.gov/events/month/2026-09/


5. Hispanic Heritage Month Celebrations – Across South Florida

Dates: September 15–October 15
Why it’s special: South Florida celebrates Hispanic and Latino culture through live music, food, dance, art exhibitions, performances, and community events throughout the region.
Learn more:
https://www.miamiandbeaches.com/events


6. Ultracon Comic Con – West Palm Beach

Dates: September 18–20
Why it’s special: A major pop-culture convention featuring comics, cosplay, collectibles, celebrity guests, artists, vendors, gaming, and entertainment. The tri-county event calendar confirms Ultracon activities for September 18–19.
Learn more:
https://ultraconofsouthflorida.com/


7. Clean Culture: SoFlo Showdown – West Palm Beach

Date: September 19
Why it’s special: A South Florida automotive gathering bringing together customized cars, car culture, entertainment, and enthusiasts at the South Florida Fairgrounds.
Learn more:
https://www.southfloridafair.com/events


8. Don Pasquale – Miami Beach

Date: September 19
Why it’s special: Florida L’Opera & Zarzuela presents Donizetti’s famous comic opera Don Pasquale, offering a cultural night out in Miami Beach. The performance begins at 7:30 p.m.
Learn more:
https://events.miamibeachfl.gov/events/month/2026-09/


9. Boca Raton Dog Shows – West Palm Beach

Dates: September 26–27
Why it’s special: Dog lovers can see a variety of breeds competing in shows and events during a full weekend dedicated to canine competition.
Learn more:
https://www.southfloridafair.com/events


10. Lincoln Road Farmers Market – Miami Beach

Dates: Sundays throughout September
Why it’s special: One of Miami Beach’s favorite weekend markets features fresh produce, flowers, specialty foods, local vendors, and the lively atmosphere of Lincoln Road.
Learn more:
https://events.miamibeachfl.gov/events/month/2026-09/


11. Miami Spice Restaurant Months – Greater Miami

Dates: Through September 30
Why it’s special: One of South Florida’s biggest annual dining promotions gives food lovers the chance to experience special multi-course menus at participating Miami restaurants.
Learn more:
https://www.miamiandbeaches.com/deals/spice-restaurant-months


12. Dine Out Lauderdale – Greater Fort Lauderdale

Dates: Throughout September
Why it’s special: Participating restaurants across Greater Fort Lauderdale offer special menus and dining experiences, making September a great time to discover new local favorites.
Learn more:
https://www.visitlauderdale.com/events/annual-events-festivals/


13. Delray Summer GreenMarket – Delray Beach

Dates: Saturdays throughout September
Why it’s special: A great local weekend activity featuring fresh produce, artisan products, food, and local vendors in Delray Beach. The current South Florida calendar lists the market on September 12, 19 and 26.
Learn more:
https://downtowndelraybeach.com/greenmarket


14. Cuerda & Clave at The Betsy – Miami Beach

Dates: Sundays throughout September
Why it’s special: The Betsy Piano Bar hosts a recurring evening of Latin-influenced live music in the heart of South Beach. Admission is free, making it an easy addition to a Miami Beach weekend.
Learn more:
https://events.miamibeachfl.gov/events/month/2026-09/


15. The Bass Free Community Day – Miami Beach

Date: September 27
Why it’s special: Families can spend an afternoon at The Bass enjoying art-making, exploration, and creative activities. Admission for the community event is free.
Learn more:
https://events.miamibeachfl.gov/events/month/2026-09/


October 2026

1. Celebrate ORGULLO – Miami & Miami Beach

Dates: Select dates in October
Why it’s special: A celebration of Hispanic, Indigenous, and LGBTQ+ culture featuring art, music, food, community gatherings, and special events throughout Greater Miami.
Learn more:
https://www.miamiandbeaches.com/events/annual-events


2. West Palm Beach Antiques Festival – West Palm Beach

Dates: Beginning October 2
Why it’s special: One of the region’s established antiques events brings together dealers and collectors offering vintage furniture, jewelry, art, collectibles, and unique finds.
Learn more:
https://www.southfloridafair.com/events


3. Passport to Pours – Boca Raton

Date: October 3
Why it’s special: Mizner Park Amphitheater becomes an international tasting destination with country-inspired food and drinks, entertainment, and live music.
Learn more:
https://www.thepalmbeaches.com/events


4. Miami Carnival – Miami

Dates: Early October; main Carnival weekend October 10–11
Why it’s special: One of South Florida’s largest Caribbean celebrations features elaborate costumes, soca and Caribbean music, J’Ouvert festivities, food, dancing, and the spectacular Parade of Bands.
Learn more:
https://miamicarnival.org/


5. Fright Nights – West Palm Beach

Dates: Select nights throughout October
Why it’s special: The South Florida Fairgrounds transforms into a huge Halloween attraction with haunted houses, scare zones, carnival rides, games, and spooky entertainment.
Learn more:
https://myfrightnights.com/


6. Oktoberfest of the Palm Beaches – Lake Worth Beach

Dates: October 9–11 & October 16–18
Why it’s special: One of South Florida’s biggest Oktoberfest celebrations features authentic German food and beer, traditional music and dancing, carnival rides, vendors, and family entertainment.
Learn more:
https://americangermanclub.org/oktoberfest/


7. Miami Oktoberfest – Miami

Dates: October 9–11 & October 16–18
Why it’s special: The German American Social Club brings traditional Oktoberfest fun to Miami with German food, beer, music, dancing, and cultural entertainment.
Learn more:
https://gascmiami.org/


8. FLOCK-toberfest – Delray Beach

Date: October 10
Why it’s special: THRōW Social brings Oktoberfest fun to downtown Delray Beach with live music, themed drinks, games, competitions, costumes, and a lively party atmosphere.
Learn more:
https://downtowndelraybeach.com/events


9. Pumpkin Fest – Jupiter

Date: October 10
Why it’s special: Harbourside Place welcomes fall with a family-friendly pumpkin festival featuring seasonal activities and waterfront fun. The 10th annual Pumpkin Fest appears on the current South Florida family calendar for October 10.
Learn more:
https://harboursideplace.com/


10. Redland International Orchid Festival – Miami

Dates: October 16–18
Why it’s special: A three-day celebration featuring rare and exotic orchids, international growers, beautiful displays, and opportunities to purchase unique plants.
Learn more:
https://www.redlandorchidfest.com/


11. Spookyville – West Palm Beach

Dates: Select dates in October
Why it’s special: Yesteryear Village becomes a kid-friendly Halloween destination with trick-or-treating, costumes, entertainment, games, and seasonal activities in a historic setting.
Learn more:
https://www.southfloridafair.com/spookyville


12. Brazilian Festival – Broward County

Date: October 24
Why it’s special: A major celebration of Brazilian culture featuring live music, samba, food, dance, entertainment, and a lively South Florida festival atmosphere.
Learn more:
https://www.visitlauderdale.com/events/annual-events-festivals/


13. Lincoln Road Farmers Market – Miami Beach

Dates: Sundays throughout October
Why it’s special: Spend a Sunday strolling Lincoln Road while shopping for fresh produce, flowers, artisan foods, and other local products in the heart of Miami Beach.
Learn more:
https://events.miamibeachfl.gov/


14. Ocean Drive Promenade Music Series – Miami Beach

Dates: Sundays throughout October
Why it’s special: Free outdoor concerts near Lummus Park combine live music with the Art Deco architecture, palm trees, and oceanfront atmosphere of South Beach.
Learn more:
https://www.oceandrivearts.com/


15. Halloween & Fall Festivals – Across South Florida

Dates: Throughout October
Why it’s special: Pumpkin patches, hayrides, harvest festivals, costume contests, trick-or-treating, haunted attractions, and seasonal food bring fall fun to Palm Beach, Broward, and Miami-Dade counties throughout October.
Learn more:
https://www.thepalmbeaches.com/events

November 2026

1. Fort Lauderdale International Boat Show – Fort Lauderdale

Date: November 1 (final day; event runs October 28–November 1)
Why it’s special: The world’s largest in-water boat show takes over Fort Lauderdale with superyachts, boats, marine technology, accessories, demonstrations, and luxury waterfront experiences across multiple locations.
Learn more:
https://www.flibs.com/


2. NASCAR Championship Weekend – Homestead

Dates: November 6–8
Why it’s special: NASCAR’s Championship Weekend returns to Homestead-Miami Speedway, with three days of high-speed racing culminating in the Cup Series Championship. It’s one of South Florida’s biggest sporting events of the month.
Learn more:
https://www.homesteadmiamispeedway.com/


3. Boca Raton Wine & Food Festival – Boca Raton

Date: November 7
Why it’s special: A culinary celebration bringing together food, wine, chefs, tastings, and entertainment for an upscale evening in Boca Raton.
Learn more:
https://bocaratonwineandfoodfestival.com/


4. Miami Beach Polo World Cup – Miami Beach

Dates: November 12–15
Why it’s special: World-class polo meets the beach as professional players and horses compete directly on the sands of Miami Beach. The combination of sport, ocean views, fashion, and social events makes this one of November’s most distinctive events.
Learn more:
https://www.miamipolocup.com/


5. Miami Book Fair – Downtown Miami

Dates: November 15–22
Why it’s special: One of the country’s major literary festivals brings hundreds of authors and presenters to Downtown Miami for talks, readings, book signings, cultural programs, family activities, and more. The popular Street Fair takes place November 20–22.
Learn more:
https://miamibookfair.com/


6. Miami Book Fair Street Fair – Downtown Miami

Dates: November 20–22
Why it’s special: The final weekend of Miami Book Fair turns the streets surrounding Miami Dade College into a huge outdoor celebration with booksellers, authors, food, entertainment, shopping, and Children's Alley activities for families.
Learn more:
https://miamibookfair.com/


7. Little Haiti Book Festival at Miami Book Fair – Miami

Dates: November 21–22
Why it’s special: Part of Miami Book Fair’s ReadCaribbean programming, this cultural event highlights Caribbean literature and voices through discussions, authors, storytelling, and other programming.
Learn more:
https://miamibookfair.com/


8. Lincoln Road Farmers Market – Miami Beach

Dates: Sundays throughout November
Why it’s special: Spend a Sunday strolling one of Miami Beach’s most famous pedestrian streets while shopping for fresh produce, flowers, specialty foods, plants, and locally sold products.
Learn more:
https://events.miamibeachfl.gov/events/month/2026-11/


9. Ocean Drive Promenade Music Series – Miami Beach

Dates: Sundays throughout November
Why it’s special: Free outdoor concerts bring live music to the heart of South Beach, combining cultural performances with Ocean Drive’s Art Deco architecture and oceanfront setting.
Learn more:
https://www.oceandrivearts.com/


10. The Bass Free Community Day – Miami Beach

Date: November 29
Why it’s special: The Bass invites families and children of all ages for a free afternoon of art-making, exploration, and creative activities at one of Miami Beach’s best-known contemporary art museums.
Learn more:
https://thebass.org/


11. Hamilton – Miami

Dates: November 10–22
Why it’s special: The award-winning Broadway musical Hamilton comes to South Florida in November, combining hip-hop, R&B, jazz, and traditional musical theater to tell the story of Alexander Hamilton. The November calendar currently lists performances beginning November 10.
Learn more:
https://www.browardcenter.org/


12. O.A.R. & Gavin DeGraw – Hollywood

Date: November 13
Why it’s special: O.A.R. and Gavin DeGraw bring a night of live rock and pop music to South Florida, making this a strong November pick for concertgoers.
Learn more:
https://www.seminolehardrockhollywood.com/entertainment


13. MOMIX: Botanica – South Florida

Dates: November 21–22
Why it’s special: MOMIX combines dance, acrobatics, imaginative costumes, lighting, and visual illusions in Botanica, a theatrical production inspired by the natural world.
Learn more:
https://www.browardcenter.org/


14. Cirque Dreams Holidaze – Fort Lauderdale

Dates: November 27–29
Why it’s special: Kick off the holiday season with an elaborate combination of circus arts, acrobatics, music, costumes, and holiday characters. It’s especially good for families looking for a Thanksgiving weekend activity.
Learn more:
https://www.browardcenter.org/


15. Thanksgiving Weekend & Holiday Kickoff Events – Across South Florida

Dates: November 26–29
Why it’s special: Thanksgiving weekend marks the start of South Florida’s holiday season, with tree lightings, holiday markets, seasonal entertainment, family activities, and festive displays beginning across Palm Beach, Broward, and Miami-Dade counties.

Learn more:
https://www.thepalmbeaches.com/events

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