Things to Do in Jacksonville - October 2019

Posted by Donny Mak on Tuesday, October 1st, 2019 at 10:08am.

October is a busy time in Jacksonville! With the weather cooling down, event season is in full swing. We've rounded up some of our picks for the month of October; let us know what you're checking out this month!

October 4th – Let’s RAP: First Friday at Clover & Woolly

Riverside Avondale Preservation will be hosting their monthly First Friday event at Clover & Woolly Salon from 5-7pm on October 4th. This free neighborhood event is a fantastic chance to get to know local businesses and mingle with your neighbors.

You will be able to enjoy light-bites, beer and wine, and live music by Alaina Colding.


October 5th – River City Pride Parade and the 5 Points Pride Block Party

The River City Pride Parade will take place on October 5th at 4pm at Willowbranch Park. This 3 mile parade (you can see the route here) will end at Riverside Park in 5 Points.

The 5 Points Pride Block Party, hosted by River City Pride, the Five Points Merchant Association, Manifest Distilling, and Aardwolf Brewery, will run from 12pm-10pm. The Block Party will feature live music, local merchants, food vendors, and games! You can view the full entertainment schedule here.


October 5th – Oktoberfest on Main Street

Springfield’s Main Street businesses are hosting their annual Oktoberfest on Main Street block party! Joi the fun on October 5th rom 1-9pm on Main Street for a day filled with festivities. You’ll be able to enjoy food trucks and traditional German fare, local bands, German music, craft beer, vendors, and games.

This is a free event that the whole family can enjoy! Learn more about the event.


October 12th – A Night Under The Stars – Slow Fish Dinner

Join Slow Food First Coast and Riverside Avondale Preservation for a fundraiser dinner at the home of Wayne Wood and Lana Shuttleworth. Proceeds from the evening will go to Riverside Avondale Preservation.

Farm partner Conagree and Penn and Manifest Distilling will join featured Riverside Avondale restaurants Biscottis, Restaurant Orsay, Black Sheep Restaurant, and Southern Roots for an evening of delicious food and libations.

Guests will also enjoy live music from Arvid Smith and The New Moon Ramblers.

Tickets are $125 each and are available here


October 26th – 3rd Annual Murray Hill-O-Ween

The Murray Hill Preservation Association will be hosting the popular Murray Hill-O-Ween on October 26th from 4-8pm.

This community event features live music, food trucks, vendors, a beer garden,  and a kids zone! The parade will begin at 7pm.

Visit the official website.

October 30th – Music on Main: MJbaker

The Springfield Preservation and Revitalization Council (SPAR) will be hosting their popular Music on Main event again in October. This free, family-friendly event takes place in Sesquicentennial Park at 1527 North Main Street. This month’s featured artist is MJbaker.

Attendees can enjoy food from local food trucks Kaboom Kababs and Manny’s Cuban Food Truck. There will also be beer and wine available for purchase. Food and drink purchases will be available starting at 5pm, and the music will begin at 6pm. Learn more about the event here.

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