Located about 25 minutes northeast of Orlando in Seminole County,  Winter Springs is referred to as “The Sleeping Giant” because of its size. Recently named one of the “Best Places to Live” by CNN Money Magazine, Winter Springs sits central Florida’s technology corridor.

The area was inhabited by Native Americans prior to European colonization. A Spanish colony from 1513 – 1763, Florida came under British possession in 1763 and was returned to the Spanish in 1783. In the early 1800’s a New York merchant, Moses Levy, acquired the land that sits on the southern banks of Lake Jesup as part of a lumbering and land trade with the Spanish. The United States acquired Florida in 1821, taking over the land grants. The Spanish grants were ultimately returned to Moses Levy and others in 1852 when the plots were revised by the courts and the area was opened to settlers.

Winter Springs, FL

By 1865 the first wharf and general store were constructed on the southern shore of Lake Jesup. The wharves along the lake (Jesup is one of Florida’s largest lakes) spurred on industries like logging, lumber, sawmills and turpentine stills.

In 1957 the land was assessed for financial value and the surveyors, Raymond Moss and William Edgermon ended up purchasing the land under the name North Orlando Company. Incorporated in 1959 as the Village of North Orlando, the city started out with roughly 300 residents.

Florida Technical University opened its doors in 1968 and later became the University of Central Florida, the nation’s third largest university. The development of an adjacent research park and the emergence of both the aerospace and defense industries in the 1970’s contributed to the ongoing growth of residential neighborhoods.

As the population and industries grew, so did the community amenities and nearby attractions, like the Walt Disney theme parks, making Winter Springs a premier destination.

Our Favorite Things to Do in Winter Springs Florida

Our mini guide to Winter Springs will help you discover this lovely, tree-lined city in the heart of Central Florida.

Nightlife Winter Springs

If its nightlife you’re after, Winter Springs has plenty to offer. Whether you are a wine connoisseur, appreciate a good craft beer, or want to kick up your heels on the dance floor, there’s enough variety to keep you busy.This list of must-visit hot spots will help you plan your nightlife adventure!

 

Red Cypress Brewery

At Red Cypress, the beers are proudly Florida born and brewed. Opening its doors in 2015, the owners of Red Cypress have a passion for craft beer and a passion for adapting the West Coast beer culture to the Sunshine state. Brew masters use locally sourced ingredients like orange peel and name their brews in homage to the legends and tales of Florida. Devil’s Chair, anyone?

Although they don’t serve food, they do allow you to bring in food from the nearby restaurants or food trucks. Not sure what to drink? Try a flight. We hear the Hollow Earth Bourbon Barrel Stout is legendary. Be sure to grab a growler or two to take home!

855 E. State Rd 434 Winter Springs, Florida

(407) 532-0341

 

Spill Wine and Beer

Looking for a great neighborhood bar with a quaint feel? Spill Wine and Beer fits the bill. Offering a small wine list and a nice selection of beer, it’s a relaxing atmosphere to wind down, listen to live music and enjoy an appetizer… Who doesn’t love a nice wine and cheese pairing?! There is seating both indoors and out, with a nice fire pit for chilly evenings. Spill is known for its friendly and welcoming atmosphere, so expect to meet a lot of regulars here.

1196 Tree Swallow Dr #1314 Winter Springs, Florida

407- 278 – 8219

 

Buchanan’s

Buchanan’s is a great place to go for a game of pool or a refreshing cocktail. The newest entry in the live music scene, Buchanan’s has a large dance floor and also hosts Corn Hole, giant Jenga, and Beer Pong competitions. There is also a separate indoor smoker’s lounge, keeping the main room smoke-free.

290 E State Road 434 Winter Springs, Florida

(407) 542-7919

Locally Owned Eateries

Winter Springs may be a small city but it is big on flavor. You won’t find the latest food trends in Winter Springs but what you will find is locally-owned, authentic, cuisine celebrating the different cultures that make up the tapestry of the city. Whether you are in the mood for fine dining or a casual family-style experience, rest assured that the city of Winter Springs will deliver (literally in some cases!). Here are some of our favorite food choices …

Stefano’s Trattoria

If you like homestyle, authentic Italian food then look no further! This is a family-friendly, casual atmosphere serving up large portions of some of the best Italian food in the area. Voted the best Italian food in al of Central Florida, Stefano’s was started by local restauranteur Stefano LaCommare who originally hails from Sicily. The food here bursts with flavor and the staff will treat you like a member of the family. This is a five-star experience without the five-star price tag.

1425 Tuskawilla Road Winter Springs, Florida

(407) 659-0101

 

Corfu Greek Restaurant

Serving up old world Greek dishes that are made from scratch, this family-owned eatery feature some of the best tasting Greek food in the Orlando area; don’t let the strip mall location fool you. Lunch and dinner are the main focus here with a breakfast option only served Thursday – Sunday. Portions are always generous and prices always reasonable. Try popular appetizers like the Spanakopita, Tzatziki or Hummus to the Charbroiled Octopus, Whole Fried Calamari and Fried Smelts. The menu at Corfu has no shortage of authentic and flavorful options. The lunch menu includes the classic Greek gyro sandwiches as well as a treat for vegetarians with their own souvlaki. They have great choices for the kids as well with chicken tenders with fries and penne pasta with red sauce. And there is a nice selection of Greek wine and beer to wash it all down.

124 W State Rd 434 Winter Springs, Florida
(407) 542-1814

 

Casey’s Grill

Casey’s is classic American bar food in a casual environment. Think wings, great burgers and cold beer! In addition to the wings and burgers there is lots of standard fare to be found on their menu including salads and sandwiches. Entrees range from fish and chips to catch of the day. Generous portions, drink specials and lots of tvs for all of your game day watching!

1335 Tuskawilla Rd Winter Springs, Florida
407-696-0533

Play Outside

Winter Springs provides ample opportunity to spend a quiet day surrounded by nature. With 13 gorgeous parks and never-ending tree-lined streets, you’ll find an abundance of outdoor activities for every age here. These are some of our favorite ways to spend a day outside in Winter Springs.

 

Soldier Creek Park Mountain Bike Trail

This is a fun 2.6 mile trail, good for both beginners and experienced riders. With elevation changes, wooden bridges, and tree cover for most of the trail, this is a great year-round place to explore on two wheels. The trail follows the Soldier Creek so there is plenty of sightseeing along the way. Offering riders choices of easier of more challenging paths, you can also walk the path if mountain biking is not your forte’.

2400 State Rd 419 Winter Springs, Florida
(407) 665-2180

 

Spring Hammock Preserve

One of the most beautiful places to hike in the Orlando area, Spring Hammock Preserve is a 1500 acre preserve that houses some of the oldest cypress trees in all of Florida. Here, you’ll also find lots of trails, a glistening spring and the Environmental Studies Center which is used to teach grade school children about environmental studies. There’s also a boardwalk that leads out to Lake Jesup.

Whether you travel here by car, bike or on foot be sure to bring your camera! The preserve is worth a visit year-round.

General Hutchison Parkway Winter Springs, Florida
407-349-0769

 

Central Winds Park

Central Winds Park is open all year long from dusk to dawn and is considered a local gem. In addition to a large soccer field, the park also has ball fields for baseball and softball, and a large three-story playground perfect for the kids of all ages. Separate pavilions provide shade for picnic tables, complete with grills, and there’s a lovely nature trail for anyone interested in observing local wildlife.

100 East State Road 434 Winter Park, Florida
407-327-6599

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