Vacations in Florida are typically infused with sunshine and coastal beaches. But land-locked Orlando, best known for its abundance of world-class theme parks, is the most visited destination in the state. Should your idea of an enjoyable getaway eschew both beaches and theme parks, your time will be much better spent across town in Winter Park. Discover the Park Avenue District, a beautifully revitalized Main Street community, celebrated for its impeccable style and local charm.
What Makes “The Avenue” So Alluring?
The Park Avenue District (known simply as the Avenue) is the centrally located commercial quarter in Winter Park. Planned in 1882 by real estate investors Loring Chase and Oliver Chapman, it was envisioned as a retreat for wealthy Northerners seeking refuge from wintry months. Over time, the town has become famous for its arts and cultural attractions, numerous parks and gardens, authentic dining destinations, and unique shopping experiences.
It’s also a product of Main Street America. Founded in 1980 under the National Trust for Historic Preservation, the organization has supported the revitalization of cherished neighborhoods, downtowns, and commercial districts across the country. As a Main Street community, the Avenue celebrates its distinctive, time-worn character through the adaptive reuse of historic spaces. It is an exciting, warm, and welcoming place where people have come together to live, work, and thrive.
Ride the Rails, Kick Back, and Relax
The legendary “Floridian,” operated by Amtrak, originates in Chicago. It subsequently winds its way through the farmlands and rural communities in Indiana, Ohio, and the Allegheny Mountains, then onwards into Pittsburgh and Harper’s Ferry. It continues along the historic B&O line through the Potomac Valley into Washington, D.C., and southward towards its final destination of Miami.
Along the way, the train makes a stop in my town, Jacksonville, Florida. My friends and I decided that a two-hour ride on the rails would make our carefree day trip to the Park Avenue District exciting. At the same time, we would avoid the headaches, frustrations, and monotony of freeway driving. Riding the rails would also give us the opportunity to delight in the constantly changing landscape. With views of lush farmland, undeveloped forests, quaint small towns, and glimpses into rural living, these are all experiences we would have missed from the road.
Where to Start in Winter Park – So Many Choices
Having visited the Avenue once before during a work-related trip to Orlando, I was excited to return. While I knew there were sights to investigate and noteworthy restaurants to enjoy, there would be far too many destinations to experience in just one day. This meant we’d have to prioritize our activities and make the most of our limited time in town.
When we arrived at the Winter Park station, we disembarked into a stunning, Craftsman-style building with paths leading directly into the Avenue’s beautifully manicured, 11-acre Central Park. Since our agenda prioritized eating and drinking, we went in search of coffee and pastries.
Having previously identified AJ Chocolate House and Cholala Fine Pastries at opposing ends of the Avenue, and the Croissant Gourmet Bakery close to where we stood on E. Morse Blvd., we chose the convenience of the bakery.
As we approached the counter, it became apparent that making a decision would be challenging. Should we try the chocolate éclairs or jalousies (a type of puff pastry filled with almond cream and raspberry)? Perhaps the croissants (filled with Bavarian cream and berries), assorted macarons, or one of several varieties of Danish pastries would be better? We all picked something different, exchanged bites, and began to realize just how well our first culinary encounter turned out. We agreed that coffees and treats from the other two shops, time permitting, would be welcomed later in the day.
Fresh Air and Sunshine. What’s Not to Like?
Refreshed by caffeine and sugar, we set off for an hour-long cruise, operated by Scenic Boat Tours on Lake Osceola. We could not have asked for a better morning. Cruising in an open-air pontoon boat under clear blue skies, every seat was a window seat. We floated across lakes, navigated narrow canals, and enjoyed the lush tropical gardens that pushed out to the water’s edge.
While the flora and fauna were enchanting, it was the unmistakable signs of wealth that were most remarkable. This was evident by the uninterrupted presence of oversized and luxurious estates at every turn.
High Noon and Time for Lunch
As we wandered, we came across a few places that seemed like worthwhile destinations for lunch. Some had intriguing menus, inviting outdoor patios, and artfully decorated interiors. Others were serving some highly impressive dishes. We knew that whichever we chose, we were in for a delightful dining experience.
Among them were Prato, a stylish contemporary Italian restaurant, and the Briarpatch, another contemporary setting that specializes in American cuisine with a Southern influence. There was also the New General Cafe, a charming cafe whose menu boasted a blend of wellness and flavor, and Bosphorous, an Anatolian/Turkish venue festooned with alluring, brightly colored Turkish lamps.
We agreed that, while all of these places were appealing, Bosphorus would provide a more adventurous culinary experience. Interested in a lighter lunch but eager for variety, we selected the Mixed Appetizer, a plate that exceeded our expectations. It included hummus, baba ganoush, sautéed eggplant, muhammara (a red pepper and walnut spread), ezme (a tomato and pepper relish), tarama (a fish roe spread), haydari (a yogurt dip), and setinyagli yaprak dolma (stuffed grape leaves). Accompanied by a warm, freshly baked, impressively large lavash, coupled with a steady supply of cocktails, life was good.
Impressive Collections of Art, History, and Culture
Faced with too many museums to visit in just one day, our group split up to pursue individual interests, agreeing to reconvene for drinks and nibbles at the end of the day.
I had time to visit both the Charles Hosmer Morse Museum of American Art as well as the Winter Park History Museum.
Tiffany Lovers, Head to the Morse Museum
The Morse Museum is arguably the most prestigious destination on the Avenue, home to the world’s most extensive collection of works by Louis Comfort Tiffany. From room to room, there were pieces in every medium from every period of his life. Being familiar with Tiffany’s lamps and stained glass creations, I was amazed to see such diversity in his work.
If you’re a history buff, you’ll enjoy the Winter Park History Museum. Small in size but broad in scope, there’s plenty on display that illuminates the important milestones of this community.
With time running short, the Rollins Museum of Art, featuring a varied collection of more than 6,000 works, would have to wait until another visit.
A Meal Near the Museum
As museums began to close, we realized there wasn’t enough time for a proper meal before we caught our train home. This meant that the elegant, Japanese-inspired, progressive tasting menu served at Ômo by Jônt (an offshoot of the Michelin-starred Jônt in Washington, DC) would have to wait. Similarly, the unquestionable appeal of Ava Mediterragean, The Chapman, and The Wine Room, all featuring creatively inspired menus, inviting dining spaces and well-stocked bars, would have to be earmarked for another visit as well.
Having noticed Blu on the Avenue earlier in the day, we commented on its light, bright, and casual vibe. This is where we enjoyed our last meal of the day. With happy hour underway, we enjoyed a few cocktails along with some mussels and calamari. We were also impressed by their Conch Fritters, fresh, hot, crispy, and loaded with conch.
We Could Have Stayed Longer
Although we contemplated an overnight stay, we had a train to catch. For next time, we’d have two accommodations within the Park Avenue District to consider, each with its own distinctive charm and character.
If you prefer a boutique hotel with the look and feel of history, then the Park Plaza Hotel is the place. Built in 1922, it’s the oldest business in Winter Park, and it is directly opposite Central Park, overlooking Park Avenue. Apart from its historic charm, there are only 28 rooms, allowing you to receive wonderfully personalized attention. Additionally, a few of their rooms feature private balconies, offering a wonderful view of the Avenue. It’s been said that the Christmas season is one of the loveliest times to stay at the hotel. Should you reserve one of their balcony rooms, and there are events in the park, you’ll have a ringside seat for the festivities.
The Alfond Inn, opened in August 2013, is the newest hotel in the neighborhood. Just a couple of blocks off the Avenue, it has become a popular gathering spot for both visitors and the community. Operated as an extension of the Rollins Museum of Art, it features colorful installations, eye-catching artworks, and a bright, casual vibe. This aesthetic permeates its public spaces, beautifully appointed spa, and all of its guest rooms. While considerably larger and more luxuriously appointed than the Park Plaza Hotel, everything comes together to create a distinctive and undeniably enjoyable experience.
One Day Isn’t Nearly Enough
From the moment we stepped off the train, it was clear that the Park Avenue District would be an exciting and enjoyable place to visit. As we returned to the station for our train ride home, we were already looking forward to another visit. One day may not have been nearly enough, but it was certainly a wonderful start.
To learn more about Jeffrey Spear or read his food and travel-related stories, visit SpearWrites.
