Wine & art events in Orlando - Orlando on the Cheap

There’s always a reason to celebrate in Orlando, giving life to monthly food, wine and art festivals. Each month you can enjoy a variety of reoccurring community events such as outdoor festivals, art walks, live music and social events at museums. Experience the cultural side of Orlando while you mix and mingle at these special happenings around town.

Monthly food, wine & art festivals in Orlando

1^st Thursdays at Orlando Museum of Art
The first Thursday of each month, the museum showcases a new theme of art by local artists accompanied by live music, a cash bar and café with selections by area restaurants. Tickets are $15 and include admission to the museum’s featured exhibitions. Parking is free at Orlando Lock Haven Park.

Art & Music in the Park & Food Truck Bazaar
Spend an evening at the beautiful Lake Concord Park in Casselberry enjoying live music, artisan booths and a variety of culinary flavors from 15 food trucks. Held the second Friday of every month from 6 p.m. to 9 p.m. Free admission and parking.

Lake Mary WineART Wednesdays.

Lake Mary WineArt Wednesday
On the first Wednesday of every month from 5 p.m. to 9 p.m., Lake Mary WineArt Wednesday features local artists, food trucks and a beer and wine garden. Stroll along the sidewalk lined with displays by local artists, sip on wine and listen to live music in Central Park. Entry is free.

Thornton Park Wine & Art Walk
On the second Thursday of every month, celebrate the arts with an evening of food, wine, shopping and showcases by Orlando-based artists. For $10 (pre-sale price), you’ll receive a wristband, wine glass and a map of 20 locations where you will be greeted with a complimentary pour of wine.

You might also be interested in: free outdoor movies in Orlando.

Sanford Art Walk
The Historic Sanford Welcome Center invites you to the Sanford Art Walk, a juried art show in the Historic Sanford Welcome Center, and a walking tour of the art venues located in historic downtown Sanford. Mingle with Central Florida artists at the Sanford Art Walk on the third Saturday of every month from 6 p.m. to 9 p.m. in downtown Sanford.

Alive After 5
Alive After 5 is Central Florida’s largest recurring monthly street party with live music, local artists, food and beverage sampling in the beautiful historic town of Sanford. It is scheduled for the second Thursday of each month from 5 p.m. to 8 p.m. Free admission.

Sanford Block Party
Drink in the street, dance, shop vendors and celebrate in this beautiful downtown area. Fourth Saturday of the month from 5 p.m. to 11 p.m.

Music at the Casa
Casa Feliz in Winter Park opens its doors on Sunday afternoons from 12 p.m. to 3 p.m. for live music and free tours of the historic house and James Gamble Rogers II Studio. Bring along a picnic to enjoy in the beautiful flower gardens. Entry is free, but a $5 donation is suggested to support programming.

2nd Friday Art in the Gallery
Go to beautiful downtown Mount Dora for a Friday night full of art and acoustic music. Second Friday of the month, 6 p.m. – 9 p.m.

First Fridays Baldwin Park
Venture through the heart of downtown Baldwin Park to meet 70 local artisans of all genres while also shopping at the local businesses. This free sidewalk festival is held the First Friday of every month from 5:30 p.m. to 9:30 p.m., and is both family and pet friendly.

Rhythms at the Roost
Listen to free live music outdoors at the beautiful amphitheater in Cranes Roost Park. The event is scheduled a couple times a year. The next one is September 28, 2019.

Third Thursday Gallery Hop
Hop to venues to experience artwork featuring talented and emerging Orlando-based artists. The event is free.

Art After Dark Lake Nona
Explore Lake Nona in the evening the first Friday of every month, 6 p.m. – 9 p.m. Featuring artists, food, wine and entertainment.

Fridays on the Plaza
Enjoy live music every Friday night on the Plaza in downtown Winter Garden.

The Food Truck Bazaar
With over a dozen starlit shindigs scheduled each month, The Food Truck Bazaar offers an atypical dining experience with a reputation for gourmet food like lobster rolls, chorizo tacos and root beer flavored cupcakes. Don’t forget chairs or a blanket; seating is typically scarce.

More Orlando events scheduled during select months:

Science Night Live
Orlando Science Center reserves an evening just for adults to play featuring grown-up inspired programming. General admission tickets are $16 (online and in advance) and food and beverages are available for purchase. The event is scheduled on select nights throughout the year.

Lakeridge Winery
Lakeridge Winery in Clermont hosts inexpensive events featuring live entertainment from local musicians, artist vendors, crafts and food. Make sure to take advantage of the complimentary wine tours and tastings.

Culture Pop!
Culture Pop at the Art & History Museums – Maitland is a social event for art lovers on select Fridays. For $15 each, you will experience art, live music and poetry. This summer, the event is a full-day affair for all ages with performances, workshops and outdoor films.

Winter Park Sip & Stroll
Sip wine paired with appetizers at more than 20 boutiques, galleries and restaurants while strolling along beautiful Park Avenue. Tickets are $25 in advance. Each reservation includes a commemorative wine glass and lanyard.

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