Discovering Historic Sanford, Florida | Wander With Wonder

Located halfway between Orlando’s theme parks and the beaches of Daytona, historic Sanford is one of Central Florida’s lesser-known gems. It makes a perfect day trip if you’re in the area, but also offers a great weekend getaway.

This charming town on Lake Monroe is filled with restaurants, antique shops, craft breweries, and nature spots. Art galleries beckon visitors, and frequent festivals fill the streets. There’s so much to explore that locals have coined the phrase “Sanfording,” which means to enjoy everything the town has to offer.

Learning About Sanford’s History

I visited Sanford years ago, but my husband had never been. One recent Friday, we decided to play hooky from work and explore this little town about 30 miles north of Orlando.

There’s lots of free public parking near the Sanford Museum, our first stop. Did you know Sanford used to be known as Celery City? After the Great Freeze of 1895 destroyed citrus crops, farmers planted celery. Sanford soon became one of the world’s biggest suppliers of celery. Located where the St. John’s River meets Lake Monroe, historic Sanford was a vibrant shipping port. In the 1800s, steamboat travel was the primary mode of transporting goods.

Historic Sanford museum

Start at the museum to learn about Sanford’s history. Photo by Kirsten Harrington

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The Historic Sanford Welcome Center is also a great place to start your visit. Located on First Street, the center has walking maps, clean restrooms, and friendly staff to answer questions. It’s also a stop on the free trolley which runs through town.

Parks and Green Spaces

The Sanford Riverwalk sits just behind the museum. This paved 4.5-mile pedestrian path is dotted with swinging benches, making it a beautiful place to stroll and enjoy lake views. Return here at dusk to experience gorgeous sunsets for which Florida is famous.

Historic Sanford swings by the lake.

Sit and swing by Sanford’s Riverwalk. Photo by Kirsten Harrington

With public binoculars mounted near the path, I spotted an alligator and two turtles swimming in the lake. While we watched, a great blue heron swooped in for a landing. A flock of Ibises splashed behind me in Fort Mellon Park. There’s also a playground, shaded picnic tables, and a splash pad nearby.

We followed the Riverwalk back toward downtown and paused at Veteran’s Memorial Park. With palm trees swaying and colorful flowers, it’s a peaceful spot to remember those who served our country.

Where to Eat and Drink in Historic Sanford

My only complaint about Sanford’s dining scene is that there are too many choices. Greek food, gastropubs, sidewalk cafes, and wine bars are just a glimpse of what’s on the menu.

Restaurants and Cafes

At lunchtime, my stomach led me to Henry’s Depot. I love food halls because they offer a snapshot of a town’s food scene.  I chose Sweet and Salty’s Huli Huli chicken because tangy and tropical grilled chicken sounded just right for a sunny, playful day.

Historic Sanford Henry's Depot food hall.

Henry’s Depot food hall offers a number of dining choices. Photo by Kirsten Harrington

Next time I want to try the Old Jailhouse, a scratch kitchen that served as the Seminole County Jail from 1914 to 1959. How often can you say you got to eat behind bars?

Historic Sanford Jail House restaurant.

You can dine behind bars at The Old Jailhouse Restaurant. Photo by Kirsten Harrington

Hollerbach’s German Restaurant is a must-try for schnitzel and live accordion music. And I love the family-friendly concept of the Yardery. Inspired by combining “yard” with “eatery,” this outdoor restaurant features a tire swing, corn hole, and ladder toss. You can eat, drink, and play in the yard!

Sweet Treats

Every good meal needs a sweet ending. Simply Homemade 1913 hit the spot with a mini key lime Bundt cake. They have a “Cake it Forward” program where you can leave a tip so someone else can enjoy a free goodie. How cool is that?

If one dessert isn’t enough (hey, I’m not judging), visit Wondermade. Order the s’mores on a stick-fluffy marshmallow paired with frozen chocolate pudding. They’ll toast it while you wait.

Craft Breweries 

Since it was five o’clock somewhere, it was time for a beer at one of historic Sanford’s many breweries. At Celery City Craft, I chose a flight of citrus-infused Florida suds to sip on the outside patio.

Historic Sanford beer flight.

Celery City Craft beer flight with citrus-infused flavors. Photo by Kirsten Harrington

Beer enthusiasts can hit five other craft breweries in a few short blocks, including Wop’s Hops Brewing. Sanford’s first microbrewery is located in the historic Stokes Fish Market Building, which still sports the market’s original mural. 

Historic Sanford’s Art Scene

I loved peering down the alleys and spotting hidden murals, like little presents waiting for me to discover. There’s color everywhere, from red brick roads to green and yellow building facades. Planters full of flowers decorate the streets, adding to the cheerful mood.

Another colorful spot is Jeanine Taylor Folk Art, home to eight working artists, each with their own studio. Stepping through the doorway to each gallery really allowed me to focus on the unique style of each artist.

Historic Sanford art gallery.

Jeanine Taylor Folk Art hosts eight artists’ studios. Photo by Kirsten Harrington

The weekend of my visit was the “Love Your Shorts” film festival, showcasing short films from around the world at the Ritz Theater. I’ll mark my calendar to see it next year. I’ll also keep an eye on the schedule for the Theater West End, which offers a full lineup of musicals, plays, and comedy shows.

Where to Shop in Historic Sanford

If I’m going to play hooky, I’m certainly spending part of the day shopping. Sanford’s compact downtown made it easy to duck in and out of antique shops, clothing stores, and markets.

Wandering up and down First Street, you’ll find Magpie’s Modern General Store, with thoughtfully sourced quirky gifts, many locally produced. The Treehouse Antique Store is packed with collectibles, vintage hats, jewelry, and all sorts of treasures I wanted to take home.

One of my favorite stops was Magnolia Square Market. I headed straight for the marzipan chocolates while my husband checked out the beer selection at this German delicatessen. Next time I’ll bring a cooler and fill it with imported cheese and sausages before we leave.

Historic Sanford cheese and sausage in a German deli.

Magnolia Square Market sells German sausages and cheese. Photo by Kirsten Harrington

I didn’t need a dirndl and my husband wouldn’t be caught dead in lederhosen, but we had fun taking a selfie in front of the costume display at  Hollerbach’s Outfitters, which sells traditional German clothing. 

Exploring Beyond Downtown

The Barbara-Lee is an authentic sternwheeler with massive wooden paddle wheels and fancy wrought iron railings. It sits in the marina, ready to take passengers on a voyage back in time. The St. Johns Rivership Company operates the lake cruises, complete with dinner and live music.

Historic Sanford paddle wheel boat.

The Barbara-Lee offers lake cruises on a vintage-inspired sternwheeler. Photo by Kirsten Harrington

You can also visit the Central Florida Zoo & Botanical Gardens. There’s a free shuttle from downtown. For a wilder animal encounter, Airrow Boat Tours cruise the backwaters of St. John’s River. Keep your eyes open for alligators, otters, and wild boars in their native habitat.

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Where to Stay in Historic Sanford 

Lodging options in Sanford consist mostly of Airbnbs, including an adorable tiny famous houseboat parked in the marina. Nicknamed “Downtown Dharma,” this rental earned fame on an episode of HGTV’s Tiny House Hunters. With a flat-screen TV, granite kitchen, and a front porch perfect for admiring sunsets, this petite palace books up quickly. Be sure to reserve in advance.

Historic Sanford tiny houseboat on the lake.

Tiny houseboat Downtown Dharma floats in the Sanford marina. Photo by Kirsten Harrington

Insider Tip: Instead of staying overnight in Sanford, stay at The Alfond Inn in Winter Park, just 20 miles away. The SunRail commuter train connects these two charming small towns. Once you arrive in historic Sanford, take the free shuttle to downtown.

“Well, I have to say this has exceeded my expectations,” my husband said after we spent a lovely day shirking responsibility to wander through all the wonders historic Sanford has to offer. Our outing reminded me that in addition to beautiful beaches and family-friendly attractions, Florida’s historic towns are also full of adventure. When planning your next trip to Florida or another destination with a small-town vibe, let Wander with Wonder be your guide.

Located halfway between Orlando’s theme parks and the beaches of Daytona, historic Sanford is one of Central Florida’s lesser-known gems. It makes a perfect day trip if you’re in the area, but also offers a great weekend getaway.

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Discovering Historic Sanford, Florida

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