Maitland's two biggest nights of the holiday season land back to back this year. Steeln' Peaches, a hometown band that plays the jam-band southern rock of the Allman Brothers, headlines a free concert in Independence Square on Friday, December 4, and the city's Season of Light fills Lake Lily Park with a tree lighting, a snow slide and fireworks the next evening, Saturday, December 5.

Both are run by the City of Maitland, both are free, and both sit within a short walk of City Hall in the small Orange County, Florida, city on Lake Maitland between Winter Park and Altamonte Springs.

Friday, December 4: Steeln' Peaches in the Square

The concert runs from 6 to 9 p.m. in Independence Square, the park beside Maitland City Hall at 1776 Independence Lane. It is this month's edition of the city's Getdown Downtown Party in the Square, the monthly downtown party, and the city has dressed it for the season with thousands of holiday lights, food trucks, drinks, vendors and entertainment for children.

The band recreates the sound the Allman Brothers made famous: long electric guitar solos, piano, percussion and soulful vocals. Admission is free. Bring chairs or blankets for seating; parking is available around the event site, according to the city.

Saturday, December 5: Season of Light at Lake Lily Park

Season of Light is Maitland's annual holiday celebration, and it runs from 5 to 8:30 p.m. at Lake Lily Park. The evening opens at 5 p.m. at the park's north stage with the official holiday tree lighting, led by city officials, the Maitland Middle School band and Santa.

From there, the park fills with holiday lights, photos with Santa, a large snow slide, carnival games, crafts for kids, food, vendors and holiday music. The fireworks start at about 8 p.m. over the park.

Every Sunday: the farmers market

The same lakeside park holds the Maitland Farmer's Market every Sunday from 9 a.m. to 1 p.m. Vendors sell food, crafts, local products, plants, flowers and produce, with live music provided by Performing Arts Matter. With Season of Light on a Saturday, the market the next morning, December 6, makes for a full weekend at Lake Lily.

On view at the Maitland Art Center

A few blocks away, Art and History Museums Maitland, at 231 W. Packwood Ave., is showing Vilomah: Against the Natural Order, an installation-based exhibition by artist Soude Dadras, through January 3, 2027. The main campus includes the Maitland Art Center, which the museums describe as greater Orlando's only National Historic Landmark, along with the Maitland History Museum and the Telephone Museum. The museums answer questions at 407-539-2181.

Getting there

Lake Lily Park is in the center of Maitland, and Independence Square is beside City Hall at 1776 Independence Lane. Maitland's city calendar, at maitlandfl.gov, lists each event; the city moved its website to that address from itsmymaitland.com, and both still work.

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