Best Fall Date Ideas In Orlando 2022

Best Fall Date Ideas In Orlando

Even the “cooler” fall nights in Orlando are crisp. It’s perfect for a date night including wine sampling, seeing art and enjoying the cool weather. A cool fall night is also perfect for cuddling and getting cozy with a special someone. At Park Ave Magazine, we compiled a list of some of the best fall date ideas in Orlando. There is a lot going on – from fall festivals to delicious foodie events.

The Winter Park Autumn Art Festival

Residents in Winter Park look forward to the annual Winter Park Autumn Art Festival every year, and has been a tradition for the past 50 years. The Winter Park Autumn Art festival features a roster of local artists, and is the only juried fine art festival exclusively featuring Florida artists. The Winter Park Chamber of Commerce hosts the festival on the second weekend of October every year. This is a community oriented sidewalk show that is held right on Park Ave. The festival boasts visual art and live entertainment that is perfect date for you and your partner. The best part is, that admission is free.

The 2022 Winter Park Autumn Art Festival will be located on Saturday, October 8th and Sunday October 9th. The festival is held in beautiful Central Park located along historic Park Avenue in downtown Winter Park.

Ukraine Ballet (Aug. 27, 2022)

Going to the Ballet is one of the most romantic date night ideas. You and your partner can dress to impress and enjoy a lovely evening of ballet dance. The National Ballet of Ukraine from the Taras Shevshenko National Opera and Ballet Theater is going to be at Steinmetz Hall, part of the Dr. Phillips Center for the Performing Arts. Their performance will be highlighting Ukrainian culture and include excerpts from several ballets, accompanied by beautiful orchestral music from the Orlando Philharmonic Orchestra.

Dr. Phillips Center, Haddock Family Foundation, Kathy Morgan & Marty Rubin and Rosen Hotels & Resorts. This means 100% of sponsorships and tickets sold will go directly to charities providing humanitarian assistance and emergency medical aid to Ukrainian citizens, refugees, and veteran services.

Purchase Tickets Here

Dazzling Nights at Harry P. Leu Gardens (Select Nights, Nov. 25, 2022 – Jan. 1, 2023)

The Dazzling Nights at Harry P. Leu Gardens is produced by Creative City Project. It is back for it’s 3rd year, and it is bigger and even more interactive than ever before. Dazzling Nights is an all-ages holiday event that transforms the 50-acre Harry P. Leu Gardens into a stunning Winter Wonderland featuring a million dazzling lights, shining forests, magical displays, music and beautiful sculptures. There are new additions for 2022 that include character meet-and-greets, magical displays, a yeti playground, music and beautiful sculptures.

Thornton 2nd Thursday Wine & ArtWalk

The Thornton 2nd Thursday Wine & ArtWalk is a monthly event that takes place on – you guessed it – every 2nd Thursday of the month. The Wine & ArtWalk takes place in the Thorton Park district and includes wine tastings from participating bars and restaurants throughout the district. There is always live music and art vendors as well.

September 8, 2022, 6:30-9:30pm
October 13, 2022, 6:30-9:30pm

Weekends at The Winery at Lakeridge Winery

Located in Clermont, Lakeridge Winery hosts “Weekends at the Winery”. Patrons can enjoy the expansive vineyard, sample delicious food and wine in the outdoor bar and lounge outside. This event is free and you can bring your own lawn chairs. “Weekends at the Winery” also includes a schedule of live entertainment. Spend your next date night sampling offerings from the outdoor wine bar as well as seasonal drinks like mulled wine, wine slushies and sangria.

12th Annual Casselberry Food and Wine Festival

Enjoy a night of food, drink and entertainment plus a silent auction at the 12th Annual Casselberry Food and Wine Festival on Monday, November 14, 6pm – 9pm at Lake Concord Park. $30 per adult, children under 10 are free. Proceeds of our Silent Auction will be distributed back into the City of Casselberry through non-profits that help enhance our community and make it a wonderful place to live and work! Event proceeds also contribute to our annual Promote Prosperity Scholarship to local High School students.

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