Your Fall Events Guide: Delray Beach & Boca Raton 2026
One of the things I love most about being a real estate agent in South Florida is getting to tell people the truth about these communities. Not just the market stats and home values. The real stuff. The lifestyle that makes someone fall in love with a neighborhood and decide to stay.
If you have been following my blog, you know I believe the best way to get to know a place is to get out in it. Walk the streets. Grab dinner on the Ave. Stumble into live music you did not plan to hear. The events calendar in Delray Beach and Boca Raton stays packed as summer turns into fall, and I have rounded up the highlights you will not want to miss. Whether you are a current resident, a new arrival, or someone exploring the area before making the move, this is your insider's guide to where the community gathers. Many of these events take place along or near Atlantic Avenue and around Mizner Park, two areas I know well and recommend to buyers looking for walkable coastal living. I refreshed this guide with confirmed dates and new additions, so bookmark it and check back as the season unfolds.
Downtown Delray Beach & Atlantic Avenue Events
Delray Beach's downtown pulses with energy year-round. As the humidity breaks and the weather turns idyllic in September and October, the Atlantic Avenue calendar fills fast. Restaurant Month, Art Walks, the return of the GreenMarket, and the kickoff to the holiday season. Here is what is coming up.
Full Moon Yoga & Night Market
Old School Square Amphitheatre, 51 N Swinton Ave, 6:30-9:30 PM
A free community wellness evening under the stars. The night kicks off with a full moon-inspired yoga flow co-led by local instructors, followed by ecstatic dance and sound healing, all set to live DJ beats. A curated night market with local vendors runs alongside, featuring artisan goods, juice, and wellness pop-ups. Bring your own mat and bring the whole family. This is the kind of evening that makes Delray Beach feel like a small town with a big heart.
More InfoParty in Paradise: Tribute to Jimmy Buffett
Old School Square Amphitheatre, 51 N Swinton Ave, 5-9:30 PM
The Summer Sunset Concert Series wraps up with a Jimmy Buffett tribute that is pure South Florida. Bring a blanket, grab dinner from a local food truck, and settle in for an evening of feel-good music at one of Delray's most beloved outdoor venues. Free and open to the public.
More InfoBourbon Fest 2026
Warren American Whiskey Kitchen, 98 E Atlantic Ave, 4 PM
A premium bourbon and whiskey tasting experience at one of Atlantic Avenue's most popular spots. Warren American Whiskey Kitchen hosts its annual Bourbon Fest with a curated selection of fine bourbons, craft cocktails, and small-batch pours from top distilleries. Live music, food pairings, and a sophisticated yet relaxed atmosphere make this a standout late-summer event. Tickets sell fast. 21+ only.
More Info2nd Annual Kickoff Crawl Atlantic Ave
Multiple venues along Atlantic Avenue, Delray Beach
A bar and restaurant crawl along Atlantic Avenue celebrating the end of summer and the start of the fall social season. Participating venues offer drink specials, food samples, and live entertainment as you stroll the Ave. It is the perfect way to explore multiple spots in one evening and connect with neighbors and local business owners. Tickets available through participating venues.
More InfoDowntown Delray Beach Restaurant Month
Throughout Downtown Delray Beach, Kickoff event Sep 1 at The Standard, 4-7 PM
Over 50 restaurants, cafes, and ice cream shops along Atlantic Avenue and surrounding streets participate with special menus, prix-fixe deals, and exclusive offerings all month long. There is even a free Restaurant Month Pass so you can track every deal. It is the best time of year to try that place you have been eyeing or discover a new favorite spot. I tell my clients all the time: the food scene here is one of the best reasons to call Delray home.
More InfoFirst Friday Art Walk
Atlantic Avenue, Pineapple Grove & Artists Alley, 6-9 PM
September's First Friday Art Walk marks the transition into fall. The weather starts to ease up, the crowds return, and the galleries debut new collections. Over two dozen galleries, working artist studios, and cultural venues open their doors for a self-guided tour with pop-up live music, wine, and conversation. If you have not experienced a Delray Beach Art Walk yet, this is the month to start. The October edition (Oct 2) is equally vibrant as the season kicks into high gear.
More InfoCoco Market Wellness Festival
Delray Beach Amphitheatre at Old School Square, 10 AM-5 PM
A Sunday celebration of wellness, community, and conscious living. The Coco Market Wellness Festival brings together yoga sessions, meditation workshops, plant-based food vendors, artisan market stalls, and live acoustic music in the beautiful Old School Square amphitheater setting. Bring a mat, bring the family, and spend the day connecting with like-minded locals. The kind of event that reminds you why Delray Beach has become a hub for health and wellness lifestyle.
More InfoSunset Stroll at Morikami Museum
Morikami Museum & Japanese Gardens, 4000 Morikami Park Rd, Delray Beach, 5:30-8 PM
An enchanting evening at one of South Florida's most serene cultural treasures. The Sunset Stroll at Morikami Museum offers after-hours access to the acclaimed Japanese gardens as golden light filters through the bamboo groves and reflects off the koi ponds. Sip sake, explore the galleries, and enjoy the meditative beauty of the grounds during the quietest part of the day. It is the kind of refined cultural experience that appeals to clients who appreciate Delray Beach's depth beyond the beach and the Ave. Advance tickets recommended.
More Info31st Annual Downtown Delray Beach Craft Festival on 4th
NE 4th Avenue (just north of Atlantic Ave), 10 AM-4 PM both days
One of Delray Beach's most beloved traditions returns for its 31st year. Thousands of handmade crafts from local and statewide artisans, including jewelry, pottery, paintings, sculpture, folk art, clothing, and gourmet goods. Leashed dogs are welcome, admission is free, and the whole stretch of 4th Avenue transforms into an open-air gallery. It is the perfect weekend to stroll the Ave, discover something unique, and eat your way through the neighborhood.
More InfoFirst Friday Art Walk, October Edition
Pineapple Grove Arts District, Atlantic Avenue, 6-9 PM
October's First Friday Art Walk is where the season truly takes off. Cooler evening temperatures, a packed crowd of locals and visitors, and galleries showing their fall collections. Pineapple Grove becomes a block party with live music on multiple stages, pop-up wine bars, and artist demonstrations. It is the kind of warm evening that reminds you why people pay a premium to live within walking distance of Atlantic Avenue.
More InfoDelray Marketplace Music Fest
Delray Marketplace Amphitheater, Every Wednesday, 6-8 PM (Oct through Apr)
Free live music returns to the Delray Marketplace every Wednesday evening from October through April. Local bands, food trucks, outdoor seating, and a relaxed neighborhood vibe. It is the kind of weekly tradition that makes this area feel like a real community, and it is a perfect mid-week break for residents and visitors alike. Grab dinner at one of the marketplace restaurants and settle in for a sunset show. The October lineup includes The Prymates (Oct 1), The Cool Water Band (Oct 15), Mad Mellow (Oct 22), and Cover to Cover Band (Oct 29).
More InfoFLOCK-toberfest 2026
THRōW Social, Downtown Delray Beach
An annual Oktoberfest-style celebration at THRōW Social, one of downtown Delray Beach's most popular entertainment venues. Expect live music, craft beer specials, lawn games, and a lively crowd of locals kicking off the fall season. It is the kind of event where the community comes out to have fun together, and tickets go fast. A great excuse to experience the THRōW Social venue if you have not been yet.
More InfoNational Night Out at Old School Square
Old School Square, 51 N Swinton Ave, Delray Beach, 9 AM-2 PM
The Delray Beach Police Department hosts this annual community-building event at Old School Square. Meet local law enforcement in a relaxed setting, enjoy free food, see police and fire equipment up close, and connect with your neighbors. Live music, kids activities, and community resource booths make it a great Sunday morning for families. It is a reminder that the best communities are the ones where people know each other.
More InfoDelray GreenMarket Returns
Old School Square Campus, Swinton Ave & Atlantic Ave, Saturdays 9 AM-2 PM (Oct 24 through May)
The beloved Delray GreenMarket returns for its seasonal run at Old School Square with 50-plus vendors offering local produce, farm-fresh eggs, raw milk, grass-fed beef, fresh seafood, artisan baked goods, flowers, plants, and specialty items. It is a Saturday morning ritual for anyone who lives within walking distance of Atlantic Avenue, and a must-visit for buyers considering a home in the area. Grab coffee, walk the market, and see what community feels like here.
More InfoBoca Raton & Mizner Park Events
Mizner Park is the cultural heart of Boca Raton, anchoring a sophisticated calendar of events through the fall and into the holiday season. From intimate performances at The Studio to the return of the farmers markets and the annual tree lighting, here is what is on the horizon.
Seventies By the Sea
Festival of the Arts BOCA at Mizner Park
A groovy evening of 1970s music and nostalgia presented by the Festival of the Arts BOCA at Mizner Park. Part of the ongoing Summer Sips & Sounds series, this event brings together live music, wine, and the unmistakable energy of Mizner Park's outdoor setting. Great for a date night or a group outing with friends. Check the Festival website for exact venue location and ticketing details.
More InfoMizner Park Farmers & Artisan Markets
Mizner Park, 201 Plaza Real, Boca Raton — Saturdays 11 AM-6 PM, Fridays 4-9 PM, Sundays 10 AM-5 PM (Seasonal)
Mizner Park's trio of weekend markets returns for the fall season. The Saturday Farmers Market features fresh local produce, artisan foods, and specialty goods. The Friday Artisan Market brings handmade crafts, jewelry, and boutique finds under the evening lights. The Sunday market blends both farmers and artisans for a relaxed weekend closeout. Running through the cooler months, these markets are a staple of Boca Raton's luxury lifestyle and one of the best ways to spend a weekend morning strolling through Mizner Park. Check Florida Fresh Markets for exact opening dates as the season approaches.
Market InfoPassport to Pours, Boca Raton
Mizner Park Amphitheater, 4 PM, $24
An afternoon of wine, craft beer, and spirits tasting at the beautiful Mizner Park Amphitheater. With your admission, you get a tasting glass and the chance to sample from dozens of vendors while live music plays in the background. At just $24, it is one of the most affordable and enjoyable tasting events in Boca Raton. Gather a group, stroll through Mizner Park, and toast to the start of the fall season. 21+ event.
Get TicketsSouth Florida Pickle Festival
Burt Aaronson South County Regional Park, Boca Raton, 12 PM
A one-of-a-kind food festival celebrating everything pickled. The South Florida Pickle Festival features pickle-eating contests, pickle vendors of every variety, craft vendors, live entertainment, and family-friendly activities. It is quirky, fun, and surprisingly popular with locals of all ages. A great option if you are looking for something different from the usual wine-and-dine circuit.
More InfoBoca Raton Holiday Tree Lighting at Mizner Park
Mizner Park Amphitheater, 590 Plaza Real, 6-10 PM, Free
Boca Raton officially kicks off the holiday season with its annual tree lighting at the Mizner Park Amphitheater. The ceremonial lighting happens at 7:15 PM, with live music performances, snow flurries, a holiday market, craft stations, costumed characters, and Santa visits from 6 to 9 PM. Mizner Park is adorned with over 50,000 LED lights across 75 palm trees, creating one of the most spectacular holiday displays in South Florida. It is free and open to the public. Arrive early to grab a good spot.
Event DetailsLooking Ahead: Fall Highlights
A few events worth marking your calendar for as we move deeper into the season.
Boca Raton Fine Art Show
Mizner Park, Free Admission
A juried outdoor fine art exhibition featuring original works from dozens of acclaimed artists across media including painting, sculpture, photography, glass, and mixed media. Set against the backdrop of Mizner Park's Mediterranean architecture and palm-lined promenades, it is one of the most sophisticated cultural events on Boca Raton's calendar. Free and open to the public both days.
More InfoEmerald Torch Awards Gala
Eau Palm Beach Resort & Spa, 100 S Ocean Blvd, Manalapan
The premier philanthropic gala on the Palm Beach coast, this year honoring legendary developer Stephen Ross. Hosted at the oceanfront Eau Palm Beach Resort, the evening includes a cocktail reception, seated dinner, live entertainment, and an award ceremony celebrating community leadership and development. Black-tie attire. Proceeds benefit local charitable initiatives. This is the kind of event where Boca Raton and Delray Beach's most engaged residents gather to support the community in style. Tickets are limited and sell out well in advance.
More InfoBoca Raton Wine & Food Festival, A Culinary Affair
Sanborn Square Park, 72 N Federal Highway, Boca Raton, 5:30-10 PM
The 13th Annual Boca Raton Wine & Food Festival returns to Sanborn Square Park for an evening of unlimited tastings from top chefs, wineries, craft breweries, and artisanal food purveyors. The Grand Tasting event includes a VIP lounge, a culinary chef competition, a cheese village, and live music under the stars. Tickets start at $65. This is the premier food and wine event of the fall season and a favorite among Boca Raton's sophisticated dining community. 21+ event.
Get Tickets100-Foot Christmas Tree Lighting & Holiday Village at Old School Square
Old School Square, 51 N Swinton Ave, Delray Beach, Tree Lighting Dec 2
Delray Beach's most beloved holiday tradition returns. The 100-Foot Christmas Tree Lighting & Yuletide Street Festival on December 2 kicks off the season in spectacular fashion, with live music, holiday performances, Santa, and the moment the massive tree lights up the night sky. But the celebration continues all month with the Holiday Village at Old School Square, featuring ice skating, a holiday carousel, mini golf, Santa's House, and more than 60 vendors. It runs through late December. If you are thinking about making Delray Beach your home, attending this event will show you exactly what community feels like here.
More InfoMerry in Mizner Holiday Entertainment
Mizner Park, Boca Raton, Select December Evenings
Throughout December, Mizner Park comes alive with pop-up holiday entertainment under the glow of 50,000+ lights draped across the palm trees. Live music, strolling carolers, and festive performances create a magical atmosphere for an evening of shopping, dining, and holiday cheer. Grab dinner at one of Mizner Park's restaurants, browse the boutiques, and let the holiday spirit find you. It is the kind of refined seasonal experience Boca Raton does best.
More InfoLet's Explore Together
One of the best parts of my job is helping people find not just the right home, but the right community. If you are thinking about buying or selling in Delray Beach, Boca Raton, or any of South Florida's coastal communities, I would love to hear from you. Whether you are ready to start looking or just curious about the market, let's talk. I will refresh this guide throughout the season as new events get announced, so bookmark it and check back. For current market data, check out my Delray Beach market report, and if you are considering selling your Delray Beach home, I can help you navigate the process from start to finish.
Get in Touch Sales Associate · Coldwell Banker Realty · License SL3571861
Ryan Parker is a South Florida real estate agent specializing in Delray Beach, Boca Raton, Highland Beach, Gulf Stream, Boynton Beach, and the surrounding luxury coastal communities. He helps buyers, sellers, and investors make confident real estate decisions while delivering a personalized, high-touch experience from start to finish.