The Most Beautiful Small Town in Every U.S. State (That Most People Drive Right Past)

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I have pulled off the highway in more small American towns than I can count. Sometimes it’s a disappointment — a shuttered main street and a gas station. But sometimes — and this is the thing nobody talks about — it’s the best stop of the entire trip.

These are the towns in that second category. One per state. The ones worth pulling off for.

The Northeast’s Most Charming Hidden Towns

• Maine — Castine

  — A Revolutionary War-era town on a peninsula in Penobscot Bay. Federal and Greek Revival houses line quiet elm-shaded streets. The entire downtown is on the National Historic Register. The inn at the top of the hill is perfect.

• Vermont — Woodstock

  — Covered bridges, a covered iron bridge, historic Marsh-Billings-Rockefeller National Historical Park, and a downtown that looks exactly like what people imagine Vermont to look like. The Woodstock Inn is the splurge.

• New Hampshire — Meredith

  — On the shore of Lake Winnipesaukee, with independent shops, good restaurants, and the gorgeous Inns and Spa at Mill Falls. Quieter than the surrounding lake towns and better for it.

• Massachusetts — Rockport

  — A former granite-quarrying town north of Boston with a working fishing harbor, artists’ galleries, and Motif No. 1 — the most-painted building in America. Seafood chowder on the wharf.

• Rhode Island — Bristol

  — The most patriotic small town in America — it has a painted red, white, and blue center stripe down the main street that it has maintained since 1776. America’s oldest Fourth of July celebration happens here every year.

• Connecticut — Essex

  — Perennially voted the best small town in America by multiple publications. At the mouth of the Connecticut River, with a Victorian Main Street, the Griswold Inn (oldest continuously operating inn in America), and the Essex Steam Train.

• New York — Skaneateles

  — Finger Lakes village on one of the clearest lakes in America. Clean enough to supply unfiltered drinking water to Syracuse. The main street has everything: good restaurants, boutiques, a classic lakeside hotel, and boat tours.

• New Jersey — Cape May

  — The largest collection of Victorian architecture in America outside of San Francisco. Beach town at the tip of the Jersey Shore, with tree-shaded streets of painted gingerbread houses. The most underrated beach town on the East Coast.

• Pennsylvania — Jim Thorpe

  — A mountain town so dramatic that it’s been called the Switzerland of America. Victorian row houses on steep hillsides, a historic rail depot, white water rafting, and a Gilded Age opera house that still hosts performances.

• Maryland — St. Michaels

  — Chesapeake Bay maritime town with a working harbor, the Chesapeake Bay Maritime Museum, and blue crabs served at outdoor tables overlooking the water. Perfect for a weekend.

• Delaware — Lewes

  — At the mouth of Delaware Bay, with a history stretching to 1631. Historic homes, a good beach, and the Cape May-Lewes Ferry across the bay. Quieter than Rehoboth Beach next door and better for it.

The South’s Overlooked Small Town Gems

• Virginia — Abingdon

  — A mountain town in the far southwest corner of Virginia with the Barter Theatre (oldest professional theatre in America), the Virginia Creeper Trail, and a main street that looks untouched since the 1880s.

• North Carolina — Brevard

  — Gateway to Pisgah National Forest in the Blue Ridge Mountains. The town has a famous population of white squirrels — a genetic quirk — a thriving arts scene, and world-class mountain biking literally at the edge of downtown.

• South Carolina — Beaufort

  — Antebellum mansions under Spanish moss, a working waterfront on the Beaufort River, and a town so picturesque that the movie “Forrest Gump” used it as a filming location. Walking distance to everything.

• Georgia — Madison

  — Sherman spared Madison from burning during his March to the Sea because it was “too beautiful to burn” (the story may be apocryphal but the architecture is real). Antebellum homes, a historic square, and a short drive from Athens.

• Florida — Fernandina Beach (Amelia Island)

  — Florida’s most historic town. Settled under eight different flags, a Victorian Centre Street, wild horses on the north end of the island, and an uncrowded beach that makes Miami feel like another planet.

• Alabama — Fairhope

  — A bluff-top town on Mobile Bay founded as a single-tax utopian colony in 1894. The philosophy faded; the charm didn’t. Organic rose gardens on the bluff, an arts district, and a pier extending into the bay with views of the sunset.

• Mississippi — Oxford

  — Home of Ole Miss and William Faulkner. A perfect small-city square with independent bookstores, James Beard-nominated restaurants, and Square Books, one of the great independent bookshops in America.

• Louisiana — Natchitoches

  — The oldest permanent European settlement in the Louisiana Purchase territory (1714). A Cane River lakefront, Fort St. Jean Baptiste, and the original location that inspired “Steel Magnolias.” Pronounced NAK-uh-tish. You’re welcome.

• Tennessee — Jonesborough

  — Tennessee’s oldest town and the storytelling capital of America — home to the International Storytelling Center and an annual festival that draws 10,000 people to listen to professional storytellers. It sounds niche. It is spectacular.

• Kentucky — Bardstown

  — Bourbon capital of the world. The Bourbon Trail runs through here. My Old Kentucky Home State Park. The Historic Bourbon Inn. Every restaurant serves bourbon in something. Even the desserts.

• Arkansas — Eureka Springs

  — Victorian spa town built on a hillside so steep that some buildings have their entrance on different floors depending on which street you approach from. No traffic lights, no traffic grid, and an arts community unlike anything else in the region.

• West Virginia — Lewisburg

  — A Colonial-era town in the Greenbrier Valley that consistently wins “Coolest Small Town” competitions. Carnegie Hall (not that one — West Virginia’s Carnegie Hall, built in 1902), independent restaurants, and access to the Greenbrier resort nearby.

The Midwest Towns That Will Actually Surprise You

• Ohio — Granville

  — A New England-style college town (Denison University) that landed in central Ohio. Greek Revival architecture, a Main Street out of a Norman Rockwell painting, and genuinely good restaurants that have no business being this good in a town this small.

• Indiana — Madison

  — On a bend in the Ohio River, with the most intact 19th-century downtown streetscape in the Midwest. Architectural historians consider it a national treasure. Most Midwesterners have never heard of it.

• Illinois — Galena

  — Ulysses S. Grant’s hometown, preserved in amber at 1865. Rolling Mississippi River hills, a perfectly intact Victorian downtown, and Italianate mansions that would cost millions in any coastal market. Weekend getaway from Chicago.

• Michigan — Saugatuck

  — A dune-town on Lake Michigan with an art community that’s been active since the early 1900s. The Oval Beach consistently makes best-beach-in-America lists. Douglas next door is quieter and equally charming.

• Wisconsin — Bayfield

  — On the shore of Lake Superior, gateway to the Apostle Islands National Lakeshore. Apple orchards surround the town. Sea caves are kayakable in summer and ice-walkable in winter. The old waterfront inn has been there for over a century.

• Minnesota — Lanesboro

  — A bike trail town in a river bluff valley in the Driftless Area of southeastern Minnesota. No fast food, no chains, a thriving arts scene, and 40 miles of the Root River Trail from your door. The B&Bs fill up months in advance.

• Iowa — Pella

  — A Dutch settlement town founded in 1847 that still takes its heritage seriously — windmills, tulip gardens, Dutch architecture, and a tulip festival every May that draws 100,000 people to a town of 10,000. The Poffertjes (Dutch pancakes) are worth the drive.

• Missouri — Ste. Genevieve

  — The oldest European settlement in Missouri (1730) and the largest collection of French Creole architecture in North America. It’s a 90-minute drive from St. Louis and almost no one from St. Louis has visited.

• Kansas — Cottonwood Falls

  — A Flint Hills prairie town with the oldest operating courthouse west of the Mississippi (1873), a gorgeous landscape of rolling tallgrass prairie, and the Chase County Historical Society Museum. Population under 1,000.

• Nebraska — Chadron

  — Gateway to the Pine Ridge Escarpment and Fort Robinson State Park, where Crazy Horse was killed. Badlands-meets-ponderosa-pine landscape that looks nothing like what anyone pictures Nebraska looking like.

• South Dakota — Deadwood

  — Wild West history isn’t performed here — it happened here. Wild Bill Hickok was shot in a poker game in Deadwood. Calamity Jane is buried here. The town looks exactly like you’d want it to look, and legal gaming keeps it financially viable.

• North Dakota — Medora

  — At the entrance to Theodore Roosevelt National Park, a restored frontier town that was once home to Roosevelt’s cattle ranch. The Burning Hills Amphitheatre hosts a spectacular outdoor musical every summer. Absolutely stunning Badlands backdrop.

Mountain West Towns That Look Like a Movie Set

• Montana — Whitefish

  — A ski town near Glacier National Park with a downtown that has miraculously avoided the big-chain invasion. Independent restaurants, a historic train depot, and Big Mountain access. One of the most livable small towns in America.

• Wyoming — Cody

  — Buffalo Bill founded it. The Buffalo Bill Center of the West is one of the finest museum complexes in America. The Cody Stampede rodeo has run every summer since 1919. And it’s the east entrance to Yellowstone.

• Colorado — Ouray

  — A former silver mining town in a box canyon in the San Juan Mountains. Natural hot springs, Victorian architecture, ice climbing in winter, jeep trails in summer, and views so dramatic that it’s called the “Switzerland of America.”

• Utah — Moab

  — Not exactly unknown, but still a small town (population under 6,000) sitting between Arches and Canyonlands National Parks. The Colorado River runs through it. The mountain biking is world-class. The night skies are among the darkest in the U.S.

• Idaho — McCall

  — On the shores of Payette Lake in the central Idaho mountains. A genuine four-season destination where Boise families have been vacationing for generations without telling anyone else about it. The Payette Brewing Company is excellent.

• Nevada — Virginia City

  — A preserved silver mining boomtown on the Nevada desert that made Mark Twain a writer. Still inhabited, still working, with a main street full of saloons and Victorian storefronts that date to the 1860s Comstock Lode.

• Arizona — Bisbee

  — A copper mining town in the Mule Mountains near the Mexican border that became an arts colony when the mines closed. Hundreds of stairs connecting hillside neighborhoods, painted Victorian houses, underground mine tours, and one of the most peculiar and wonderful communities in America.

• New Mexico — Taos

  — A high-desert arts town that’s been drawing painters, writers, and philosophers since Georgia O’Keeffe and D.H. Lawrence in the 1920s. Taos Pueblo has been continuously inhabited for over 1,000 years. The skiing is excellent and the green chile is mandatory.

Pacific Coast Hidden Towns Worth the Detour

• California — Ferndale

  — A Victorian dairy farming town on the Northern California coast that looks exactly like a Hallmark movie location because Hallmark has filmed here multiple times. Preserved Victorian “butterfat palaces” built by wealthy dairy farmers in the 1880s.

• Oregon — Astoria

  — The oldest American settlement west of the Rocky Mountains (1811). The Goonies was filmed here. The Astoria Column sits on a hill with views of the Columbia River mouth. An arts and brewing scene that punches well above its weight.

• Washington — Walla Walla

  — Wine country that rivals Napa at a fraction of the price. Over 100 wineries in a college town with a walkable downtown, farmers markets, and genuinely excellent restaurants. One of the best-kept secrets in Pacific Northwest travel.

• Alaska — Sitka

  — Once the capital of Russian America, sitting on Baranof Island in the Alexander Archipelago. St. Michael’s Cathedral, Sitka National Historical Park, and the most dramatic small-town setting you will ever see — ocean, fjords, and volcano on the horizon.

• Hawaii — Hana

  — At the end of the Road to Hana on Maui — 64 miles of one-lane road through rainforest, waterfall, and black sand beach. The town itself is tiny, the Hana Maui Hotel is spectacular, and the journey is as much the point as the destination.

The Great Plains: Small Towns With Big Stories

• Texas — Marfa

  — A former frontier outpost in the Big Bend desert that became a contemporary art destination after minimalist sculptor Donald Judd moved here in the 1970s. The Chinati Foundation, the Prada Marfa installation, and the Marfa Lights phenomenon make this one of the strangest and most compelling small towns in America.

• Oklahoma — Guthrie

  — Oklahoma’s original capital, frozen in time at 1907 when the capital was moved to Oklahoma City. The largest contiguous urban district of late Victorian commercial architecture in the U.S. A walkable downtown that most Oklahomans don’t know exists.

How to Actually Visit These Towns (Without It Being Awkward)

Small towns require a different mindset than city travel.

• Book your accommodation first — many of these towns have 2–4 inns or B&Bs and they fill up on weekends, especially in fall
• Arrive on a weekday when possible — weekend crowds in small towns feel disproportionately large and the experience is better mid-week
• Eat at the one highly-rated local restaurant, not the chain on the highway — the local place is always the reason to go
• Talk to people. Small town locals are almost universally proud to share what makes their town special and will point you to things not in any guide.
• Plan to slow down — small towns reward wandering, not itinerary-checking
• Check festival calendars before you go — many of these towns have an annual event that transforms them and is worth timing your visit around

The best travel experiences in America are not in the cities everyone already agrees on. They’re in the towns you’ve never heard of, that you’ll spend the rest of your life telling people to visit.