Why Dunedin, Florida Was Named the Best Small Town to Live in 2026
- Natalija Ugrina
- 21 minutes ago
- 10 min read
Dunedin, Florida first came onto my radar the way a lot of unexpected places do — through a headline.
I saw it listed as one of the best small towns to live in for 2026, and I paused.
Florida has a lot of charming towns. Some are beautiful but crowded. Some are historic but sleepy. Some are fun for a weekend but don’t feel like somewhere you’d actually build a life.
So when Dunedin appeared on a national “best small towns” list, I wanted to know: Is this just another pretty Gulf Coast town… or is there something deeper here?
The only way I know how to answer that question is the same way I always do — by walking it myself.
And after spending time in Dunedin — visiting the history museum, stepping inside the Fenway Hotel, walking the marina, learning about its Scottish roots, and discovering its unexpected innovations — I understand why it made the list.
But before we get into what makes it special today, let’s talk about how it started.
The List That Put Dunedin on My Radar
When Dunedin appeared on the “10 Best Small Towns to Live in the U.S.” list, it wasn’t standing alone.
Here’s the complete lineup of towns included:
Phoenixville, Pennsylvania
West Richland, Washington
Belmont, North Carolina
Lambertville, New Jersey
Frisco, Colorado
Penngrove, California
Maplewood, Missouri
Lewes, Delaware
Campton Hills, Illinois
Dunedin, Florida
That’s a remarkable group — mountain towns, historic Northeastern gems, creative Midwestern hubs, Pacific Northwest quiet communities, and then Dunedin representing the Gulf Coast.
This wasn’t a “most beautiful beach towns” ranking.
It was a livability ranking.
And that’s a very different emphasis.
How Dunedin Was Founded
Dunedin’s roots stretch back to the mid-1800s, shortly after Florida became a state. The early settlement was originally known as Jonesboro, named after a local merchant whose general store was one of the first community centers.
In the late 19th century, two Scottish merchants — John O. Douglas and James Somerville — opened a store in the area and successfully petitioned for a post office. When it came time to choose a name, they selected Dunedin, derived from Dùn Èideann, the Gaelic name for Edinburgh, Scotland.
The town was officially incorporated in 1899, making it one of the older established communities on the Gulf Coast.
This Scottish beginning is part of what makes Dunedin feel distinct: it didn’t just grow — it arrived with identity.
From Tarpon Springs to Dunedin: Two Unique Gulf Coast Stories
Before Dunedin was on my map, another Gulf Coast town already was: Tarpon Springs.
You might remember when I explored that town — a place I came to know and write about for its vibrant Greek heritage and historic sponge industry. (If you haven’t read it yet, you can find my Tarpon Springs story here: https://www.natalijaugrina.com/post/sponges-secrets-and-suvlaki-navigating-tarpon-springs-greek-oasis)
Tarpon Springs is unique because its identity was shaped by the people who built it: Greek sponge divers who arrived in the early 1900s and transformed that little coastal town into the sponge capital of the world. Walking through Tarpon Springs feels like stepping into a Greek seaside village — with bakeries, Orthodox churches, and festivals that feel centuries old.
Dunedin’s identity is different. It didn’t arrive because of one dominant industry or one immigrant community — it evolved through layers of commerce, transportation, culture, and choice.
And that makes the contrast between these two neighboring towns fascinating. One is defined by a powerful cultural heritage that was brought here. The other is shaped by founders who brought their identity with them and made it the foundation of the place.
The Scottish Heritage of Dunedin
Dunedin’s Scottish influence isn’t superficial — it’s foundational.
Street names like Scotland Street, Highland Avenue, Aberdeen Street, and Stirling Heights aren’t coincidences. They are reminders of the town’s roots.
The Scottish cultural presence also comes alive each year in the Dunedin Highland Games, where pipe bands, clan marches, and traditional celebrations take over downtown.
Bagpipes in Florida might sound unexpected — but here, they make sense. The Scottish identity is lived and celebrated, not just marketed.
Dunedin Florida embraces its Scottish roots — from bagpipes to annual Highland celebrations.
That cultural continuity is rare and part of what makes Dunedin feel like a place with soul.
The Dunedin, Florida History Museum: Layers of Time
If you want to understand a place more deeply, visit its history museum.
The Dunedin History Museum is housed in the old train depot — a reminder that rail was at the heart of many Florida towns in the late 19th and early 20th centuries.
Inside, the museum’s exhibits narrate how Dunedin grew from a frontier settlement into a citrus hub, a maritime community, and later a cultural center.
It’s not a massive museum, but it’s rich in the kind of local story that gives a sense of continuity and authenticity you don’t get from a plaque on the sidewalk.
The Fenway Hotel and the First Radio Station in Pinellas County
One of Dunedin’s most iconic landmarks is the Fenway Hotel, a building that tells more than one story.
The hotel was originally opened in 1927, during Florida’s land boom era — a time when the state was experiencing rapid development fueled by tourism, speculation, and rail expansion. Its Mediterranean Revival architectural style reflected the glamour and optimism of that period, with arched windows, stucco walls, and waterfront positioning that immediately signaled ambition.
But what makes the Fenway Hotel historically significant isn’t just its design — it’s what happened inside.
Shortly after opening, the Fenway became home to the first radio station in Pinellas County. At a time when radio was still a relatively new and transformative technology, broadcasts were transmitted from within the hotel. This was the late 1920s — an era when radio was reshaping American culture, connecting communities, spreading news, and broadcasting live music into homes for the first time.
In fact, the Fenway’s station was one of the earliest in the broader Tampa Bay region. The hotel itself became a cultural gathering place where guests could listen to live radio programming and music performances. It wasn’t just a place to stay — it was a place to experience the future.
That detail changes how you see the building.
It’s easy to admire the Fenway today for its aesthetic — waterfront views, restored interiors, historic charm. But knowing that it played a role in early broadcasting gives it weight. It connects Dunedin to a moment when technology was transforming communication across the country.
The building has gone through periods of decline and restoration over the decades, reflecting the broader cycles of Florida’s growth and reinvention. Today, it operates as a restored boutique hotel under the Autograph Collection brand, blending modern luxury with preserved architectural character.
What I love about this piece of history is that it’s unexpected.
You don’t immediately associate a quiet Gulf Coast town with early radio innovation. Yet here it is — a 1927 hotel that helped transmit voices and music across Pinellas County nearly a century ago.
It’s another reminder that Dunedin’s identity wasn’t built solely on beaches or tourism. It participated in cultural shifts, technological progress, and regional development.
And that kind of layered history is part of what makes it more than just a pretty coastal town.
Donald Roebling and the “Alligator” Amphibious Vehicle
Here’s one of my favorite Dunedin surprises.
The town has connections to an early amphibious vehicle known as the “Alligator.” Designed by engineer Donald Roebling, the Alligator was originally created for rescue operations in swampy, hurricane-prone environments.
What’s remarkable is that this early innovation became influential in later amphibious vehicle designs — including those used by the military.
For a small town, having roots in technological experimentation and practical invention is a major character boost.
It tells you something about the people here — they weren’t just living in a coastal town. They were thinking about how to solve real-world problems.
Dunedin and Baseball
If you visit Dunedin during spring, you’ll immediately feel the town energize.
That’s because Dunedin is the longtime spring training home of the Toronto Blue Jays, a Major League Baseball team.
TD Ballpark becomes a gathering place. Locals and visitors alike gravitate toward games, lively patios, and baseball season buzz.
The presence of professional sports — even part of the year — gives the town a rhythm you don’t find in every small community.
It’s another layer of identity: quiet and calm much of the year, but alive and engaging when baseball season comes around.
Top 10 Things to See in Dunedin
If you’re visiting Dunedin for the first time — or trying to understand why it was named one of the best small towns to live in — these are the places that reveal its personality.
1. Downtown Dunedin
Downtown is the heart of the town, and what makes it feel livable rather than just picturesque. The streets are genuinely walkable, lined with independent shops, local cafés, murals, and small galleries instead of chain stores. It feels compact, friendly, and easy — the kind of place where you naturally slow down instead of rushing through.
2. Dunedin History Museum
Housed inside the former railroad depot, the Dunedin History Museum gives real context to everything you see around town. Exhibits trace the city’s development from its early settlement days as Jonesboro through its citrus farming era and maritime trade years. If you want to understand how Dunedin evolved rather than just admire it, this stop matters.
3. Andrews Memorial Chapel
Built in the late 1800s, Andrews Memorial Chapel is one of the oldest surviving buildings in Dunedin. Its simple wooden structure reflects the town’s early frontier years and offers a quiet reminder that Dunedin’s story stretches back far before the boutiques and waterfront views. It’s small, understated, and deeply rooted in local history.
4. Fenway Hotel
The Fenway Hotel isn’t just architecturally beautiful — it’s historically significant. Built in 1927 during Florida’s land boom, it once housed the first radio station in Pinellas County. Standing inside, you’re not just in a hotel; you’re inside a building that helped shape early broadcasting in the region.
5. Dunedin Marina
The marina is where Dunedin’s coastal identity feels most tangible. Boats line the water, pelicans hover overhead, and the Gulf stretches out in quiet confidence. It doesn’t feel like a flashy resort harbor — it feels like a working waterfront woven naturally into everyday life.
6. The Beatles Museum
This might be the most unexpected stop in town. The Beatles Museum houses an extensive collection of memorabilia connected to the band’s history and cultural impact. It’s a surprising reminder that even small coastal towns can hold global stories inside them.
7. Local Art Galleries
Dunedin has a thriving creative community, and you see it in its independent galleries scattered through downtown. Many showcase local and regional artists, giving the town a cultural vibrancy that goes beyond beach life. It adds another layer to why Dunedin feels alive rather than sleepy.
8. Dunedin Fine Art Center
The Dunedin Fine Art Center functions as both an exhibition space and community hub. With rotating exhibits, workshops, and classes, it reflects the town’s commitment to supporting creativity. It’s one of the reasons Dunedin consistently ranks high for quality of life — culture is accessible here.
9. Pinellas Trail
The Pinellas Trail runs directly through Dunedin, following the path of the old railroad line. Today it connects neighborhoods, parks, and downtown in a way that encourages biking and walking. It’s a perfect example of how Dunedin preserved history while adapting it for modern lifestyle.
10. Honeymoon Island & Caladesi Island
Just minutes from downtown, Honeymoon Island State Park and nearby Caladesi Island offer some of the most pristine natural coastline in the region. These barrier islands provide beaches, wildlife, and protected landscapes that feel untouched compared to more commercial Gulf destinations. Having this kind of nature so close is part of what makes Dunedin not just beautiful — but livable.
Where to Stay in Dunedin Florida
(This section contains affiliate links. If you book through them, I may earn a small commission at no extra cost to you.)
If you’re visiting Dunedin Florida — whether for a Gulf Coast getaway or to see why it was named one of the best small towns to live in — where you stay can shape your entire experience.
Here are three strong options depending on your travel style:
Fenway Hotel (Autograph Collection)
If you want to stay somewhere that feels like part of Dunedin’s story, the Fenway Hotel is the most iconic choice.
Originally opened in 1927 during Florida’s land boom, this historic waterfront hotel once housed the first radio station in Pinellas County. Today, it blends restored Mediterranean Revival architecture with modern comfort, rooftop views, and walkable access to downtown and the marina.
It’s ideal if you want atmosphere, history, and location all in one place.
👉 Book the Fenway Hotel here:
Grant Street Inn
For a more intimate and charming stay, Grant Street Inn offers boutique-style accommodations just steps from downtown Dunedin.
The property has a cozy, residential feel, making it ideal if you want to experience Dunedin Florida like a local. Its central location allows you to walk to restaurants, shops, the Pinellas Trail, and the marina without needing a car.
👉 Check availability at Grant Street Inn here:
Hampton Inn Dunedin
If you prefer modern amenities and dependable comfort, Hampton Inn Dunedin is a great option.
It’s especially convenient for families or longer stays, offering complimentary breakfast, a pool, and easy access to both downtown Dunedin and nearby beaches. It combines comfort with practicality while still keeping you close to everything that makes Dunedin special.
👉 View rates for Hampton Inn Dunedin here:
Why Dunedin Deserves the Ranking
After walking through downtown, visiting the museum, standing inside the Fenway Hotel, learning about the “Alligator,” watching the marina come alive, and feeling the pulse of baseball season, I see it clearly.
Dunedin works because:
It’s truly walkable.
It has preserved history.
It connects naturally to nature and water.
It has cultural identity rooted in real heritage.
It balances quiet life with community energy.
It feels lived-in, not manufactured.
This place feels like a place you could actually live — not just visit.
And that’s why it deserved to be on that list.
Watch My Full Dunedin Video
If you want to see what Dunedin looks and feels like through my eyes — the walking, the history, the marina, the Scottish details, and the unexpected stories — you can watch my full video here: