September might be coming to a close, but there are still plenty of events to start fall off in the funniest way possible! Make the most of the upcoming weekend by listening to live music, shopping from local vendors, or even meeting up with other dog lovers! Daniel Tosh is even in town for comedy lovers.

9.21

Downtown Jacksonville Sip & Stroll
Hit the Southbank Riverwalk on the third Thursday of each month for a lovely event full of tasty beverages, food vendors, live music, and more. Free. 5 p.m. Southbank Riverwalk,1001 Museum Cir, Jacksonville, FL 32207; downtownjacksonville.org // @dtjax

North Beaches Art Walk
Over a dozen local shops and galleries will feature work from Florida-based artists at this long running art series. See work from artists whose diverse styles and innovative approaches to their practice will amaze and inspire. Free. 5 p.m. Beaches Town Center, 0 Atlantic Blvd, Neptune Beach, FL 32266; nbaw.org // @northbeachesartwalk

9.22

Ne-Yo with Mario and Pleasure P at Daily’s Place
Ne-Yo’s Champagne and Roses tour comes to town for one night only. A stacked evening of sultry R&B and slow jams featuring special guests Mario and Pleasure P. $49.50+. 7:30 p.m. 1 Daily’s Place, Jacksonville, FL; dailysplace.com // @dailysplace

9.22 – 9.23

E.T. the Extra-Terrestrial at the Jacksonville Symphony
Witness Steven Spielberg’s iconic family film in a whole new way — projected above a symphony orchestra, who will be accompanying the action onscreen, performing the movie’s iconic score live. You’ll love it so much, we bet you’ll want to “phone home” about it! $32+. 7 p.m. 300 Water Street, Suite 200 Jacksonville, FL; jaxsymphony.org // @jaxsymphony

Jax Book Fest at the Main Library
Expanding to a two day ordeal, Jax Book Fest is back and better than ever! With special guest authors doing readings, signings and keynote discussions, plus writing workshops, lectures, and kids programming, this is the perfect event for book lovers of all ages. Free. 10 a.m. 303 N. Laura St. Jacksonville, FL; jaxpubliclibrary.org // @jaxlibrary

9.23

Wu-Tang Clan, Nas, and De La Soul at Daily’s Place
Three legends of NYC hip-hop have joined forces for one of the best tours of 2023: Wu-Tang Clan, Nas, and De La Soul’s NY State of Mind tour hits Daily’s Place this weekend. This will be one for the ages and a must-see for any hip-hop head. $49.50+. 8 p.m. 1 Daily’s Place, Jacksonville, FL; dailysplace.com // @dailysplace

Oktoberfest at Legacy Ale Works
Get in the autumnal spirit with a visit to Legacy Ale Works’ fifth annual Oktoberfest. Grab a big glass boot of beer, enjoy some brats and soft pretzels, and let the Oktoberfest vibes wash over you. Free. 12 p.m. 14965 Old St. Augustine Rd. Ste 129, Jacksonville, FL; legacyaleworks.com // @legacyale

Tails & Trails at the Jacksonville Arboretum & Botanical Gardens
Meet up with other Jacksonville dog lovers for a special day of trail hikes and other activities geared towards dogs and the ones who love them! Plus, plenty of pet vendors, pools, and other surprises will keep you and your pooch busy between hikes. $10. 11 a.m. 1445 Millcoe Road Jacksonville, FL; jacksonvillearboretum.org // @jacksonvillearboretum

9.24

The 904 Pop Up at Seawall Pavilion
The largest pop up event in North Florida returns for another killer event— and it’s the final one for the year! Shop local by checking out one-of-a-kind pieces from home grown clothing, beauty, and art vendors. Free. 11 a.m. 75 1st St N, Jacksonville Beach, FL; 904popup.com // @904popup

Daniel Tosh at the Moran Theater
Comedian Daniel Tosh has a (well deserved) reputation for boundary pushing, pitch black humor. His Sweet T tour comes to the Jacksonville Center for the Performing Arts’ Moran Theatre for one night only! $42+. 7 p.m. 300 West Water Street, Jacksonville, FL; jacksonvillecenterfortheperformingarts.com // @jaxperformingartscenter

 Note: Most descriptions courtesy of event hosts and edited for clarity.