Coolest of Jax Preview

Access this tour for free

Experience this tour for free. Available through our app.

Download or access the app

iOS Android Web

Coolest View of Jax: Baker Point

Baker Point Park at the Ortega River Bridge has the coolest views of downtown Jacksonville. The Ortega River Bridge is the most active drawbridge in he state of Florida, because it is very low and there are multiple marinas that serve as a safe port for vessels coming from all over the east coast of the United States. The bridge connects to the historic neighborhood or Ortega featuring some of the most elegant waterfront homes in the city. On the other side of the road is Stinson Park, cruise around the etire park before heading back into Avondale.

Coolest Architecture: Avondale

Avondale has the coolest architecture in Jacksonville. This neighborhood is home to the most architecturally diverse architecture in the entire state of Florida. This is the Knauer House featuring a grand entrance that looks like it’s from the Vienna, Italy. The architect, Jefferson Powel spent a great deal of time in Italy before returning to Jacksonville to design this and other magnificent homes in the area. If architecture is your thing, exit out of this tour and download the Architectural Gems route to discover more of our most treasured masterpieces, or stay on this tour and take a slow ride down St Johns Avenue where you will see many more homes of Avondale, a planned community that was developed in the 1920’s and is listed on the national registry of historic places.

Coolest Ride Along the River

Welcome to John Murray Forbes Park and this lovely ride along the river as you head toward your next stop, a Castle. Continue heading towards downtown.

Coolest Castle: Cheeks Mansion

This is CHeek's Mansion, also called The Maxwell House because it was built for Mr Leo Cheeks who started what is now Maxwell House Coffee. The remains of the original cement dock are still there...the dock was also a platform for croquet. Learn more about this and other homes in the neighborhod on Art Bikes guided tours that focus on the art, architecture and history of Jacksonville. Continue along River Blvd toward Memorial Park.

Coolest Park: Memorial Park

Dedicated on. Christmas day 1924, Memorial Park opened as a memorial to those who served and died in WWI. The park was designed by the Ulmstead Brothers, Frederick Ulmstead designed Central Park in New York. 4 generations of Ulmsteads designed over 6,000 public parks in America. Head along Riverside toward the Cummer, your next destination will take you over the St Johns River, look for the pedestrian signal to safely cross the street.

Coolest Bridge to Bike: The sUP

Welcome to the Shared Use Path, The sUP which opened in April of 2023 and connects 5 Points to San Marco. There are several pull-outs at the top of the bridge where you can pause and look in the river for dolphin. Continue along the bridge into San Marco and bear right at the bottom as you continue to the South Bank Riverwalk.

Coolest Tree: Treaty Oak

Treaty Oak" is said to be the oldest living thing in Jacksonville - some say it is 800 years old, some say a mere 200. In order to get an accurate age, you would have to bore into the tree's core which would ultimately kill this massive Live Oak. Tales of ``treaties'' signed under its massive limbs date to the Dixieland amusement park that occupied the site after the turn of the century, Jessie Ball duPont saved the big tree from destruction in the early 1960s by buying the land around the tree and donating it for a park that now bears her name.

Keep riding toward the river river as you head to Friendship Fountain.

Coolest Fountain: Friendship Fountain

Friendship Fountain is back! After 3 years of renovation, the fountain resumed delighting people with dancing water and magical lights in February of 2024. When the park opened in 1965, the Fountain of Friendship was the world’s largest and tallest fountain, capable of spraying 17,000 gallons of water a minute to a height of 120 feet. Accentuated by colored lights at night, it soon became a popular tourist destination and local recreation site. The Museum of Science and History is closing as it prepares to move to a new location on the other side of the river. Friendship Fountain has a brand new playground and has all kinds of events including live music, yoga and light shows. Click Here to see whats happening in the park! The park provides a wonderful view of downtown Jacksonville and access to the Southbank Riverwalk that opened in 1985. There are nightly light shows at the fountain every half hour starting at 7 PM

Coolest Bookstore: Chambline's Uptown

This is the coolest bookstore in Florida! Chamblin’s is a treat for any book lover, it’s a literal book mine with treasures to discover around every corner. Chambline’s Uptown has been a staple of downtown Jacksonville 2006 but its first chapter started in 1976…As you will see, its organized chaos and there is no central inventory of their titles—but ask the folks at Chambline’s what you are looking for and chances are they will guide you to it! You are right around the corner from James Weldon Johnson Park, Jacksonville’s oldest park and city hall in the St James building a stunning prairie style architecture which is likely the largest prairie style in the world. Check this page for a link of things to do downtown, or continue along to Springfield and the Phoenix Arts District.

Coolest Murals: Phoenix Arts District

Welcome to The Emerald Station and the murals of the Phoenix Arts District. The Phoenix Art and Innovation district is one of the newest and most vibrant scenes in all of Jacksonville. Explore this area to see an incredible collection of public art all along 14th street and toward your next destination. Phoenix hosts several mural meet ups and is a hub for local artists. You are riding through the historic neighborhood of Springfield, check out the links to learn more and enjoy your ride through the porches of Springfield, Jacksonville’s original neighborhood.

Coolest Ice Cream: Dreamette

Dreamette Originally known as Creamette when it opened in 1948, they changed to Dreamette in 1969 and is the oldest ice cream shop in town. Dreamette continues to be reconized as one of the best ice cream shops in Florida, The original Dreamette is located in Murray Hill, close to where your started in Avondale. We wanted to drop you by here as you start your journey vack toward downtown, more parks and more discovery on the Coolest of Jax tour.

Coolest New Park: Lift Ev'ry Voice

Welcome to Lift Ev'ry Voice Park and the first completed piece of the Emerald Trail. Lift is a tribute to the Johnson Brothers, James Weldon and Rosamond Johnson who wrote "Lift E'vry Voice and Sing" right here in Jacksonville in the year 1900. This song is now celebrated as the Black National Anthem. You are in the neighborhood of LaVilla, a historically black neighborhood that was filled with music, commerce and fashion at the turn of the century. Follow the trail along and over the bridge with murals that tell the story of LaVilla as your ride along into the historic neighborhood of Brooklyn.

Coolest Hipsters: 5 Points

5 Points is Jacksonville's very own Bohemian neighborhood with great coffee shops, bars and local merchants. At the turn of the century, this was an important trolly stop, now its a. great place to shop and dine. Follow along to the next stop as we talk about Jacksonville's Rock n Roll history. You will proceed along Oak Street which has a dedicated bike lane.

Coolest Music History: Allman Brothers House

Welcome to the Allman Brothers House! This is the home where Greg and Duane live in 1969 and 1970 as they filled out the rest of their band. Jacksonville has a rich and vibrant music history, from James Weldon Johnson to Ray Charles, the Allman Brothers and Lynyrd Skynyrd, who went to high school just a few blocks from here. We proudly say this is the neighborhood where Southern Rock n Roll was born. Continue along back to the bike shop, we will be glad to pour you a cold beer!

Tucker Cycles

Tucker Cycles is the world-wide headquarters of Art Bikes Jax! The world's only Art Bikes! Holt Tucker is Jacksonville's most sought-after bike mechanic and helps to keep our Art Bikes fleet in top shape. Come in for bikes, accessories, service and awesome Tucker Cycles merch! You can also pick up historic Jacksonville merch!

Coolest of Jax
Cycling
15 Stops
3h
25km
0:00
/
0:00