Southampton, NY

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• Top 6 Suburbs on Long Island

  Currently #5 · score 0

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• Garden City, NY

  Garden City was founded in 1869 by dry-goods magnate Alexander Turney Stewart as one of the first planned residential communities in the United States, laid out with wide tree-lined boulevards and consistent architectural standards at a time when most American suburban development was still happening in a far more ad hoc, unplanned fashion. That founding vision has proven remarkably durable — Garden City's zoning and architectural review standards have kept much of the village's original late-19th and early-20th-century character intact for over 150 years, and the Cathedral of the Incarnation, built as Stewart's own memorial and completed in 1885, remains one of the village's most visible historic landmarks. The Long Island Rail Road's Hempstead Branch connects Garden City to Penn Station in roughly 35 to 40 minutes, and the village's proximity to Roosevelt Field — one of the largest shopping malls in the country, built on the site of the airfield Charles Lindbergh departed from in 1927 for his transatlantic flight — has made it a genuine retail and commercial hub for the surrounding Nassau County area, not purely a bedroom community. Home to Adelphi University and consistently ranked among Long Island's top public school districts, Garden City's combination of a deliberately planned, well-preserved village core and strong institutional anchors has made it one of the most consistently sought-after and highest-priced residential markets on all of Long Island.

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• Huntington, NY

  Huntington sits on Long Island's North Shore in Suffolk County, and its harbor-town character — a genuine working harbor alongside a dense, walkable downtown — has made it one of the more culturally active suburban centers on the island, with a concentration of live-music venues, restaurants, and an art cinema that draw visitors from well beyond the immediate area. Poet Walt Whitman was born in Huntington in 1819, and the Walt Whitman Birthplace State Historic Site preserves his childhood farmhouse as a museum and cultural center — a point of genuine literary significance for a town that's otherwise best known today for its downtown nightlife and harbor-adjacent parks. The Long Island Rail Road's Port Jefferson Branch serves Huntington station with service to Penn Station in roughly an hour, a longer commute than many closer-in Nassau County suburbs, which has helped keep Huntington's character somewhat more independent of a purely Manhattan-commuter identity than towns closer to the city line. Huntington's combination of harbor access, a dense and active downtown arts and restaurant scene, and a meaningful literary legacy tied to Whitman has made it one of the more culturally distinctive entries among Long Island's North Shore communities, drawing residents specifically for its town character rather than commute time alone.

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• Great Neck, NY

  Great Neck occupies a peninsula on Long Island's North Shore in Nassau County, and its geography and Gold Coast-era mansions are widely believed to have inspired the fictional "West Egg" in F. Scott Fitzgerald's The Great Gatsby — Fitzgerald himself lived nearby in the early 1920s while the novel's setting took shape, and Great Neck has leaned into that literary association as part of its local identity ever since. The community's public schools are consistently ranked among the strongest on Long Island and in New York State more broadly, a reputation that's drawn a substantial and long-established Persian-Jewish community to the area over the past several decades, alongside longer-standing Jewish and broader immigrant communities that have made Great Neck one of the more religiously and culturally diverse high-income suburbs in the region. The Long Island Rail Road's Port Washington Branch connects Great Neck to Penn Station in roughly 30 minutes, one of the faster rail commutes available anywhere on Long Island, a real practical advantage layered on top of the area's literary cachet and school reputation. Great Neck's combination of a genuine Gatsby-era literary legacy, a fast direct rail commute, and consistently top-ranked schools has kept it one of the most enduringly desirable — and expensive — residential markets on Long Island's North Shore for the better part of a century.

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• Port Washington, NY

  Port Washington sits on Manhasset Bay in Nassau County, and the adjacent Sands Point peninsula — home to former Gold Coast estates including one, Falaise, built for Harry F. Guggenheim — is widely cited alongside Great Neck as part of the real-world inspiration behind the mansion-lined shorelines of The Great Gatsby's fictional East and West Egg. The hamlet's downtown sits directly on the water, with a harborfront park and a Main Street built around the Long Island Rail Road terminus, giving Port Washington a genuinely walkable, marina-adjacent character that's distinct from the more purely residential feel of many nearby North Shore communities. That LIRR branch, the Port Washington Branch's namesake terminus, delivers commuters to Penn Station in roughly 35 to 40 minutes, and because the line terminates in Port Washington rather than continuing further east, the town functions as something of a natural gateway point between Nassau County's North Shore and the rest of Long Island. Sands Point Preserve, the former Guggenheim estate now operated as a Nassau County park, opens its Gold Coast-era mansion grounds and waterfront trails to the public, giving Port Washington residents direct access to a piece of the same Jazz Age estate landscape that helped define the area's literary and architectural legacy nearly a century ago.

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• Rockville Centre, NY

  Rockville Centre sits on Long Island's South Shore in Nassau County, and its village center — built directly around the Long Island Rail Road station — has developed into one of the more walkable, restaurant-dense downtown districts among South Shore suburban communities, a contrast to the more purely residential character of some neighboring towns. The Long Island Rail Road's Babylon Branch connects Rockville Centre to Penn Station in roughly 30 to 40 minutes depending on the specific train, a genuinely convenient commute that's helped sustain steady demand for the village's housing stock even as prices across the broader Nassau County market have climbed substantially over the past two decades. The village operates its own municipal electric utility, RVC Light and Power, a distinction it shares with only a small number of other communities in the state — a legacy of an early-20th-century decision to keep utility service under local control that residents and village officials still point to as a source of lower electric rates than most surrounding areas served by the regional utility. Rockville Centre's combination of a walkable, transit-oriented downtown, a reliable direct rail commute, and locally controlled utility service has made it one of the more consistently recommended South Shore alternatives to the North Shore's higher-priced Gold Coast communities for buyers prioritizing value alongside a genuine walkable village feel.

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• Portland, OR

  Portland's unofficial civic slogan, "Keep Portland Weird," reflects a genuine and long-cultivated civic identity built around independent business, eccentric public art, and a resistance to homogenized national chain culture — one the city has largely succeeded in preserving even as it's grown substantially over the past three decades. The city was among the first in the country to adopt a formal urban growth boundary, established in 1979 under Oregon's statewide land-use planning law, deliberately limiting suburban sprawl and concentrating development within a defined area — a policy choice credited with helping preserve the region's surrounding farmland and forest while also being blamed, by some critics, for contributing to rising in-city housing costs over subsequent decades. Portland has built one of the most bike-friendly infrastructure networks of any major American city, with an extensive network of dedicated bike lanes and one of the highest rates of bicycle commuting in the country, complementing a food-cart culture so extensive that entire city blocks are sometimes organized as semi-permanent food-cart "pods" rather than traditional storefronts. Powell's City of Books, occupying an entire city block downtown, is one of the largest independent bookstores in the world by inventory, and its continued success alongside a broader culture of independent coffee shops, breweries, and record stores has made Portland one of the most frequently cited examples nationally of a mid-sized American city building an identity deliberately around independent, small-scale local business rather than national chains.

• Raleigh, NC

  Raleigh, named directly for English explorer Sir Walter Raleigh, was founded in 1792 specifically to serve as North Carolina's state capital, and it forms one corner of the Research Triangle alongside Durham and Chapel Hill — a name coined in the 1950s around the deliberate creation of Research Triangle Park, a large research and technology campus built specifically to anchor the region's universities to private-sector employers. That triangle of institutions — North Carolina State University in Raleigh itself, Duke University in Durham, and the University of North Carolina at Chapel Hill — has fed a sustained, decades-long pipeline of research talent into the technology, biotech, and pharmaceutical firms clustered in and around Research Triangle Park, giving the metro area an economic base built substantially around higher education and applied research. That foundation has translated into consistently strong job growth over the past two decades, with Raleigh regularly appearing near the top of national rankings for tech-sector and biotech employment growth, and rankings, drawing a steady wave of relocating professionals from higher cost-of-living metro areas along both coasts. Raleigh's combination of a genuine research-university economic base, comparatively lower cost of living than many coastal tech hubs, and a growing downtown restaurant and arts scene has made it one of the more consistently recommended mid-sized American cities for movers specifically seeking Sun Belt job growth without the highest-tier housing costs of Austin or Denver.

• Minneapolis, MN

  Minneapolis is known as the "City of Lakes," with thirteen lakes located within the city limits itself, and the Chain of Lakes park system connecting several of the largest of them via a continuous public trail has made lake access — for swimming, running, biking, and paddling — a defining part of daily life for residents in a way few other major American cities can match. The city built one of the most extensive enclosed pedestrian skyway systems in the world beginning in the 1960s, connecting dozens of downtown buildings via climate-controlled second-story walkways specifically to make the notoriously cold Minnesota winters more livable for downtown workers and residents — a practical piece of urban infrastructure that's become one of the city's most distinctive physical features. Minneapolis's arts and music scene has produced an outsized cultural footprint relative to the city's size — the Guthrie Theater is one of the most respected regional theater companies in the country, and First Avenue, the downtown nightclub where Prince recorded much of the concert footage for Purple Rain, remains an active and celebrated music venue decades after the film's 1984 release. Functioning as one half of the Twin Cities alongside neighboring Saint Paul across the Mississippi River, Minneapolis's combination of extensive lake access, genuinely functional cold-weather urban design, and a music and theater scene with real national reach has made it a consistent presence on "best cities to live" rankings despite a climate that's, by most measures, among the coldest of any major US metro area.

• Charleston, SC

  Charleston occupies a peninsula between the Ashley and Cooper Rivers on South Carolina's coast, and its historic district — one of the largest and best-preserved collections of pre-Civil War architecture in the country, including the iconic pastel row houses of Rainbow Row — has made it one of the most photographed and visited historic city centers in the United States. The city has topped Travel + Leisure and Condé Nast Traveler readers' polls for "best city in the United States" more times than almost any other American city over the past two decades, a sustained run of recognition built substantially on that historic architecture, a nationally regarded restaurant and culinary scene, and a walkable, cobblestone-street downtown scaled for pedestrians rather than cars. Charleston's history is genuinely complex and increasingly reckoned with directly rather than glossed over — the city was a major point of entry for the transatlantic slave trade, and the International African American Museum, which opened on the Charleston waterfront in 2023 at the site of a former slave-trading wharf, has become a significant addition to how the city presents its own history to visitors. The College of Charleston, founded in 1770, is among the oldest institutions of higher education in the country, and the city's combination of deep colonial and antebellum history, an increasingly candid public reckoning with that history's darker chapters, and a consistently top-ranked culinary and hospitality scene has kept Charleston one of the most nationally celebrated mid-sized cities in the United States.

• Denver, CO

  Denver's nickname, "the Mile High City," is precise rather than approximate — the fifteenth step of the Colorado State Capitol building is marked at exactly 5,280 feet above sea level, a detail the city has embraced as a literal point of civic identity rather than just a loose figure of speech. The city functions as the primary gateway to the Rocky Mountains for both residents and visitors, and that proximity to world-class skiing, hiking, and outdoor recreation within roughly an hour or two's drive has become one of Denver's single biggest draws for the wave of remote workers and outdoor-recreation-focused movers who relocated there in significant numbers through the 2010s and early 2020s. Denver's economy has diversified substantially beyond its historical roots in mining and energy, building genuine strength in aerospace, technology, and craft brewing — the metro area has one of the highest concentrations of breweries per capita of any major American city, anchored by the annual Great American Beer Festival, one of the largest beer competitions and festivals in the country. That rapid growth and diversification have made Denver one of the most consistently cited "best cities to live" picks in national rankings over the past decade, even as the city, like Austin, has faced real housing-affordability pressure and rising cost of living as a direct consequence of that same sustained population growth.