5 More Ways to Spend a Saturday in Winter Park

Travel outside the theme park bubble and you’ll find plenty of places where you can unwind.

One of the best, especially during the holiday season, is the city of Winter Park, just north of Orlando.

More than a century ago when the town was meticulously laid out, it was considered a winter resort, a place where snow birds from the north could hibernate during winter months.

This city of parks, lakes, world-class museums and prestigious homes maintains an old world charm that’s personified in the downtown area along Park Avenue, what many have dubbed “Little Europe.”

Along this brick-covered street you’ll find locally-owned shops, boutiques and restaurants along with popular chains you might recognize. There’s even a Pottery Barn inside an old movie house.

A few months ago, we told you about five ways to spend a Saturday in Winter Park. Things like the Morse Museum, the Farmers’ Market and the Scenic Boat Tour were all featured on the list.

Today we’re back on Park Avenue telling you about five more ways to spend a Saturday in Winter Park, from retracing the footsteps of a beloved children’s television pioneer and a hotel that has the vibe of an art museum to a shop where you can find some unique holiday decor and, I’ll let you in on a secret to my favorite burger in greater Orlando and how you too can order it.

Fans of Mr. Rogers look at the new statue of the beloved children’s television host shortly after it was unveiled on the campus of Rollins College in Winter Park, Florida.

Mr. Rogers’ Neighborhood Tour

1000 Holt Ave, Winter Park, FL 32789

We’ve told you before how Winter Park is home to one of the most beautiful college campuses in America.

Established in 1885, Rollins College is Florida’s oldest post-secondary institution.

With its main entrance across from Park Avenue, the campus covers 70 acres on the banks of Lake Virginia.

Several well-known faces have passed through this campus over the decades.

But without a doubt the name most associated with Rollins is everyone’s favorite neighbor, the man you might have watched on public broadcasting as a kid, the late Mr. Fred Rogers.

Rogers came to Rollins in 1948 as a transfer student, graduating with a degree in music composition three years later.

It was on this campus where Rogers developed his unique worldview and curated his positive attitude.

It’s also where he met his future wife, Joanne Byrd.

The couple would often return to Rollins over the decades, even becoming Winter Park snowbirds in their later years by renting a house on Lake Osceola.

While Mr. Rogers passed away in 2003, his legacy of kindness lives on every day at his Alma mater.

The college now offers a free self-guided walking tour for fans who want to explore the neighborhood that shaped Mr. Rogers.

It’s recommended you start your journey at the Olin Library where inside you’ll find a case with items that belonged to Mr. Rogers, including a sweater knitted by his mother and worn on the show, and a pair of his famous sneakers.

Other stops include a marble “Life is for Service” plaque near Strong Hall that inspired Rogers as a student and a stone on the college’s Walk of Fame positioned in front of his old residence hall.

The newest tribute to Mr. Rogers can be found in the courtyard of the historic Knowles Memorial Chapel.

Officially unveiled in October 2021, is one of the most inspiring sculptures you might ever lay eyes on. It’s called, “A Beautiful Day for a Neighbor.”

The bronze cast piece depicts Rogers surrounded by a diverse group of children with one of his favorite puppets on his hand. Near the base are lyrics from the television show’s theme song and the Neighborhood Trolley.

The back of the sculpture is truly amazing. Poking out from King Friday’s castle are characters like Lady Elaine Fairchilde and my personal favorite, X the Owl.

Designed to be an inspiration to future generations, the sculpture masterfully captures the spirit of this dearly-loved man and the lessons he taught that our society could still learn from today.

One of the many art pieces on display at The Alfond Inn at Rollins in downtown Winter Park, Florida.

Alfond Inn at Rollins

300 E New England Ave, Winter Park, FL 32789

A 3-minute walk from Rollins College across Fairbanks Avenue is a one-of-a-kind hotel that is home to an impressive art collection.

The Alfond Inn is owned and operated by Rollins with proceeds going to fund student scholarships.

Walk inside this Triple-A Diamond Rated boutique hotel and it’s like stepping into a mansion filled with beautiful art.

Over 300 paintings, photographs, sculptures and mixed media works by established and emerging artists from around the world are included in the collection.

The works were chosen because they embody the themes relevant to a liberal arts education.

Even if you’re not staying at the Alfond, you’re welcome to come in and explore the public areas where the collection resides.

Pieces are often rotated in and out, so you’re bound to see something new with each visit.

A.B. Newton and Company is one of the many locally-owned brands featured at Adjectives Market on Park Avenue in downtown Winter Park, Florida.

Park Avenue

If you’re like me and not the type to enjoy being dragged to the mall, a stroll down Park Avenue might be more to your liking.

Bordered by a shady park that plays host to concerts and art festivals, this charming street is home to dozens of locally-owned boutiques, sidewalk cafes, fine dining restaurants, art galleries with a few nationally-known brands mixed in.

We have been shoppers at the handful of Adjectives Market locations in Central Florida for years now.

While we love the Altamonte and Winter Garden storefronts, the newer location on Park Avenue has the vibe of a curated boutique you might find in Greenpoint or Williamsburg, Brooklyn.

Abby and I stopped in just as they were putting out their winter inventory and found some unique holiday items on display.

It’s an interesting shop to explore with local touches by A.B. Newton and Company and plenty of things you wouldn’t expect.

We always purchase our glasses and sunglasses from Warby Parker and the growing New York-based company recently opened a brick and mortar shop on Park Avenue at the corner of Lyman.

This sun-filled storefront gives customers a chance to try on new styles in-person rather than depending solely on home try-on, which sometimes can be limited when it comes to selection.

Looking for a bit of nostalgia or a remedy for that sweet tooth? Rocket Fizz never disappoints, especially when it comes to their large selection of unique flavored sodas and taffy.

Inside Rifle Paper Company in Winter Park’s historic Hannibal Square neighborhood.

Hannibal Square

642 W New England Ave, Winter Park, FL 32789

A couple of blocks west of Park Avenue is one of the city’s most historically significant neighborhoods, Hannibal Square.

Inside the Hannibal Square Heritage Center,visitors can learn details about how Winter Park came to be thanks to members of the African-American community who resided in this very neighborhood.

It was print shop owner Gus Henderson who in the 1880s rallied black registered voters to cast their vote to make Winter Park an official city.

Two black men from Hannibal Square went on to serve on the city council.

Today, this neighborhood is home to a number of shops, including one of Abby’s favorites - Rifle Paper Company, a lovely park with a molecular dog statue, and several places to eat.

Toasted

1945 Aloma Avenue, Winter Park, Fl 32792

Who doesn’t love a good grilled cheese sandwich? It’s nostalgic food that’s the epitome of classic Americana.

At Toasted in a strip plaza on Aloma Avenue, they elevate the grilled cheese sandwich using locally sourced ingredients prepared in-house. The result - a sophisticated sandwich with flavors that satisfy the grilled cheese purist and those with more adventurous palates.

Abby and I have been eating here for years. She usually goes for a simple grilled cheese, while I always order something that no longer is posted on the in-store menu.

It’s called the Triple B Burger. A thick patty topped with applewood smoked bacon and blue cheese on a locally-sourced bun that never falls apart. While they no longer put blue chips on the sandwich, this is still, hands down, my favorite burger in the greater Orlando area. And this coming from someone who doesn’t eat a lot of blue cheese. It truly does take the burger to a whole new level.

If you’re in the neighborhood, you have to try it. They have two other locations in the UCF area and Windermere.