100 Best Midwest Small-Town Getaways | Midwest Living

100 Best Midwest Small-Town Getaways

Midwest Living editors have been visiting the region's small towns for more than 25 years. Here are our top 100 places to escape for a little shopping, sightseeing and relaxing.
  • The Midwest's best small towns

    The Midwest has about 8,500 towns with populations less than 20,000. Midwest Living® writers and editors have been looking for the best ones since the magazine's first issue in 1987. For this list of the best small-town getaways, we added another layer of research that spanned several months and ranked towns in terms of attractions, vibe, scenery, walkability, shopping, dining, lodging, arts scene, outdoor activities, proximity to major cities, multiday potential and special events.

    We excluded suburbs, and we didn't consider livability factors such as education or employment. It took us years to compile this list of the best places to visit, but you'll only need a weekend in any of these to see why we did. (Pictured: Marshall, Michigan.)

  • Ephraim/Fish Creek, Wisconsin

    New England is known for its quaint landscapes, but the Midwest has its own coastal charm around the Great Lakes. Our top towns in Door County are the best examples of it: Ephraim and Fish Creek bookend Peninsula State Park.

    Rent bikes and ride down the coastline, check out the two towns' dozen of art galleries, or go shopping at high-end boutiques. The towns' signature meal is a fish boil, an outdoor show with flames billowing around a cauldron of whitefish, potatoes and onions. Top if off with pie made with cherries from the orchards that flourish in the peninsula's interior.

    Door County, Wisconsin

  • Petoskey/ Charlevoix, Michigan

    These neighboring resort towns along the Lower Peninsula's northwest shore began entertaining vacationers who came by steamship more than a century ago. No wonder they're so good at it, offering an ever-growing to-do list for travelers and a relaxed attitude. Petoskey climbs hills along Little Traverse Bay, and Charlevoix (pictured) nestles between Lake Michigan and Lake Charlevoix 17 miles southwest.

    The beach and harbor are steps from the 100 shops and galleries of Petoskey's Gaslight District and landmark Stafford's Perry Hotel. Charlevoix's boutiques string along the waterfront. Local restaurants, including Palette Bistro and Jesperson's (good pie!) deliver memorable meals. In the warmer months, visitors golf at the Inn at Bay Harbor, a first-class resort with courses heralded as the Midwest's Pebble Beach.

    Petoskey, Michigan

    Charlevoix, Michigan

  • Galena, Illinois

    The preservation movement in this old lead-mining town has effectively defined the trend toward small towns reinventing themselves. Framed by northwest Illinois hills, the business district's century-old buildings now house more than 90 shops filled with antiques, home accessories and art. Some 50 inns and hotels welcome travelers, and restaurants serve seemingly every taste. If Main Street or the many festivals get too crowded, escape with a hot-air balloon ride, spa treatment or pottery class.

  • Madison, Indiana

    Towering limestone bluffs and the Ohio River frame picturesque Madison, an old riverboat port of 12,400. This town is so tied to the past, 133 downtown blocks are on the National Historic Register of Historic Places, with buildings dating back to 1817. Antiques dealers fill the district, which has served as a model for preservation of other towns. A brick river walk leads visitors close to touring riverboats that regularly dock with loads of vacationers, and a stroll through Madison's hilly streets provides glimpses of lush gardens around grand old homes, some converted to inns.

    Drives out of town meander to several award-winning wineries, some of the area's best bike trails and Clifty Falls State Park, where seven waterfalls flow.

    Madison, Indiana

  • Saugatuck/ Douglas, Michigan

    These side-by-side Lake Michigan shore villages are so artsy, residents take for granted having their portraits painted. Their likenesses hang in one of the 40 galleries that liberally mingle with an appealing collection of boutiques. Visitors not only fine original art adorning studio windows, but also they get accustomed to encountering sculptures on almost every corner of Saugatuck and Douglas.

    Artists set up easels among the swimmers and sunbathers enjoying the crescent of white sand to capture Oval Beach (considered one of the county's best) on canvas. Summer also brings an acclaimed film festival and jazz- and chamber-music series.

    Saugatuck/Douglas, Michigan

  • Nashville, Indiana

    So-called progress never made it to Nashville, the seat of Brown County, a haven of hills and forests 50 miles south of Indianapolis. That's fine with the artists who live and work in studios tucked amid the town's 250 shops and the countryside. Indiana painter T.C. Steele founded the artists' colony here, drawn by the vistas that seem to spread from every hilltop. The woodsy setting around Nashville also suits hikers and others who explore nearby Brown County State Park, Indiana's largest.

    Brown County, Indiana

  • Bayfield, Wisconsin

    Lake Superior adventure awaits visitors to this town of 600 on the Bayfield Peninsula. Like jewels tossed into the sapphire water, the 22 Apostle Islands lie just offshore. On summer days, Bayfield's harbor is full of kayaks and tour boats going to and from the beaches, lighthouses and campsites in the legendary archipelago.

    More relaxed explorers ride ferries to Madeline Island, the only inhabited Apostle, which offers shops, a renowned beach, a museum and places to eat. The shops, inns and restaurants of Bayfield look down from hills along the lake. The surrounding peninsula is marked by pay-on-your-honor berry and apple stands and an absence of chain stores. Most summer nights bring performing arts under the old-fashioned Big Top Chautauqua tent.

    Bayfield, Wisconsin

  • Put-in-Bay, Ohio

    A storybook family getaway is just a ferry ride away from northwest Ohio's Lake Erie shoreline. Only boats connect South Bass Island and its town of Put-in-Bay to the mainland, so most visitors leave cars behind. That usually reduces the traffic noise among shops and restaurants to no more than the hum of golf carts and the jingling bells on rental bicycles.

    Family attractions fill the island, including museums, cave tours, fishing charters and a 1917 carousel. For the best area view, climb the 352-foot Perry's Victory and International Peace Memorial, a white column commemorating a U.S. victory in the War of 1812.

    Put-in-Bay, Ohio

  • Photo courtesy of Stillwater CVB,

    Stillwater, Minnesota

    The timber of the St. Croix River Valley on the Minnesota/Wisconsin border built the fortunes behind Stillwater's Victorian mansions, and the forest and craggy river valley still supply scenery visitors love. The town about 20 miles east of Saint Paul lures travelers with an irresistible mix: a dozen inns and a historic downtown sprinkled with antiques shops and bookstores that bring collectors from all over the world.

    Shore drives lead to notable towns, including Marine on St. Croix and Taylors Falls. Train and riverboat tours are staples. Plus, Stillwater offers one of the region's most surprising boat tours: St. Croix cruises in a gondola built in Venice.

    Stillwater, Minnesota

    Taylors Falls

  • Mackinac Island area, Michigan

    It's become a cliche to say that arriving by ferry at an island's harborside village is like stepping back in time. But it's so true at Mackinac Island that you'll wonder if the idea originated on this Gilded Age holdover. The queen of Victorian Era resorts, the white-columned Grand Hotel (left), occupies a bluff over the waters between Michigan's peninsulas.

    Because cars are banned, the signature sound is the clip-clop of horses' hooves. Visitors take carriage tours, ride bikes, taste famous fudge and tour the 1700s fort. Back on the mainland, explore the island's gateways, St. Ignace and Mackinaw City, linked by the five-mile Mackinac Bridge.

    Grand Hotel

    Mackinac Island

    St. Ignace, Michigan

  • Find history in Illinois

    Alto Pass/Jonesboro These two rustic towns provide a base for outings in southern Illinois' Shawnee National Forest (left) and a growing wine scene. Alto Pass/Jonesboro
    Bishop Hill Descendants of settlers preserve a Swedish-American Utopian community's legacy. Bishop Hill
    Alton/Elsah/Grafton Historic buildings, antiques shops and inns line the Mississippi. Alton/Elsah/Grafton
    Nauvoo You'll find restored buildings and reenactors in this onetime Mormon enclave on the Mississippi River, in addition to a winery and historic hotel. Nauvoo
    Arcola/Arthur Amish country sits nearby, so visit shops selling Amish everything or lots of places for hearty food. ArcolaArthur

  • Indiana's classic villages

    Seymour The inspiration for much of John Mellencamp's music offers an arts center (left) and hiking in the nearby Jackson-Washington State Forest. Seymour
    Chesterton Home of a Wizard of Oz museum, this town also is near Indiana Dunes. Chesterton
    Corydon Indiana's original capital has a vibrant town square, including a 55-year-old soda fountain, and it lies on the Ohio River Scenic Byway. Corydon
    New Harmony Historic buildings, an inn and labyrinth recall communal life. New Harmony
    Centerville This antiquing hotbed features buildings from the early-1800s heyday of the National Road. Centerville
    Greencastle DePauw University anchors this town near Parke County's famed covered bridges. Greencastle
    Shipshewana This epicenter of the simple farming life has hearty Amish-style food, furniture, quilts and other crafts. Shipshewana

  • Heritage and Hollywood in Iowa

    Dyersville Check out the Field of Dreams movie site (left). The baseball diamond from the movie is still there, surrounded by fields of corn. The town also has farm toy, doll and woodcarving museums. Dyersville
    Pella Go Dutch with a gingerbread-trimmed downtown, pastries, a re-created village and 80,000 tulips blooming for a festival every May. Pella
    Amana Colonies Seven villages preserve a communal society's spirit with dining, museums and shops. Amana Colonies
    Decorah Bluffs and clear streams surround a college town known for its major Norwegian-American museum and outdoor sports. Decorah
    Okoboji/Spirit Lake Outdoor activities abound near these hubs for Iowa's "Great Lakes" region. Visit small amusement parks, play a round of golf, or enjoy some water sports on the lakes. Okoboji/Spirit Lake
    McGregor/Marquette Neighboring towns are appealingly situated along the Mississippi with river views in Pikes Peak State Park. McGregor/Marquette
    Keokuk Watch for bald eagles, and see a lock and dam on the Mississippi. Keokuk

  • Kansas: History, prairie -- and shopping

    Atchison How did Amelia Earhart ever leave her pretty hometown on the Missouri? One possible answer: She never saw Nell Hill's popular home furnishing shops (left)Atchison
    Abilene President Dwight Eisenhower credited his hometown for making him who he was. Visitors can take tours of his museum, home and library, and there's also a re-created cow-town complex. Abilene
    Lindsborg This little town might be more Swedish than Sweden itself (in an old-timey way) -- with authentic crafts, foods and festivals. Its strong arts scene includes Bethany College. Lindsborg
    Cottonwood Falls At this tiny but cool base for exploring the Flint Hills, visitors find high-end lodging/dining at Grand Central Hotel and live music at Emma Chase Cafe. Cottonwood Falls
    Fort Scott Explore a frontier fort with 20-plus restored and re-created buildings. Fort Scott
    Council Grove Historic sites dot this Santa Fe Trail town, and it's only a short drive to the Tallgrass Prairie National Preserve. Council Grove

  • Michigan's landmarks and lakeshores

    Manistee The Victorian downtown connects to Lake Michigan by a boardwalk (left)Manistee
    Frankenmuth "Little Bavaria" has chicken-dinner restaurants, the world's largest Christmas store (Bronner's) and year-round festivals. Frankenmuth
    Marshall It takes a weekend to see all the significant buildings (850) in this designated National Historic Landmark District. The Honolulu House is a highlight. Marshall
    Munising This laid-back village rests next to Lake Superior and the Pictured Rocks National Lakeshore. Munising
    South Haven On the shores of Lake Michigan, this town has beaches within walking distance of downtown and inns, plus fresh foods at the edge of wine country. South Haven
    Leland/Suttons Bay On the Leelanau Peninsula near Traverse City, this area showcases the lake's bounty: fresh fish, views and local wines. Leland;  ​Suttons Bay
    Copper Harbor Along one of the region's best drives, you'll find a Lake Superior harbor and lighthouse tours. Copper Harbor
    Chesaning July's Showboat Festival brings big-name performers. Chesaning

  • Explore the Minnesota wilderness

    Ely A wear-your-hiking-boots-to-dinner spirit energizes this jumping-off point for Boundary Waters canoe trips. There are also wolf and bear centers, resorts such as Burntside Lodge (left), and authentic North Woods restaurants. Ely
    Grand Marais A onetime fishing village between the North Woods and Lake Superior draws both outdoorsy types and a big community of working artists. Grand Marais
    Northfield The town is still proud of defeating Jesse James (celebrated at a huge fall festival), with lots more going for it, including shops and two picture-perfect college campuses. Northfield
    Lanesboro This is a haven for cyclists and other lovers of the peaceful outdoors with the Root River trail, plus good food, inns and productions at the Commonweal Theatre. Lanesboro
    Nisswa Don't miss summer's weekly turtle races at this hub for the vacation area around central Minnesota's lakes. Nisswa
    Park Rapids This town is so laid-back, you wouldn't guess it's surrounded by busy lake resorts; it's also near Mississippi headwaters at Itasca State Park. Park Rapids
    Wabasha Eagle watching on the Mississippi includes the National Eagle Center; Grumpy Old Men was filmed here. Wabasha
    Red Wing This quaint Mississippi port is known for the restored St. James Hotel and tours of famous Red Wing pottery. Red Wing
    Detroit Lakes This resort town favors a folksy, relaxed mood. Detroit Lakes
    New Ulm Visitors enjoy music, festivals and shops selling imports in what the U.S. Census labeled the country's "most German city."
    Mantorville Explore historic buildings, bike the trails and watch drama at local theater. Mantorville



  • Missouri's river hamlets

    Rocheport Shops, inns and cafes cater to cyclists on the Katy Trail (left)Rocheport
    Hannibal Fact and fiction blur in Mark Twain's hometown on the Mississippi River, with tours of his home, Tom Sawyer's cave, riverboat rides and Twain shows. Hannibal
    Sainte Genevieve See amazing French Colonial architecture in one of the oldest settlements west of the Mississippi River. Sainte Genevieve
    Fulton There's an arresting vibe at Westminster College, the site of Winston Churchill's "Iron Curtain" speech and home of a Berlin Wall segment. Fulton
    Hermann It seems like you're right on the Rhine in this German village, but you're not. You're in Hermann, a hub for Missouri River wine country and cyclists' beloved Katy Trail. Hermann
    Weston This is a time capsule of a town rich in pre-Civil War history with shops, museums and old homes. Weston
    Carthage Civil War and Route 66 sites are here, as well as George Washington Carver's home. Carthage
    Arrow Rock This town is home to the 1834 Arrow Rock Tavern and the respected Lyceum Theatre. Arrow Rock
    Kimmswick Twenty-five shops and 157 people are in this Mississippi hamlet south of St. Louis; riverboat rides from St. Louis are offered in the summer. Kimmswick

  • North Dakota's wild west

    Jamestown The buffalo still roam at this frontier village full of Western history. discoverjamestownnd.com
    Medora Enjoy this western-theme-park of a town, gateway to Theodore Roosevelt National Park. Medora Musical celebrates TR's spirit. ​medora.com
    Williston See a restored frontier fort at the historic junction of the Yellowstone and Missouri rivers. visitwilliston.com
    Valley City This town of historic bridges, buildings and parks rests along Sheyenne River Valley National Scenic Byway. ​valleycitynd.org


  • Pioneer spirit in Nebraska

    Nebraska City Newcomers travel here to visit the striking Lied Lodge (left) and the farm of Arbor Day founder J. Sterling Morton. They return for shops downtown and riverboat rides in nearby Brownville. Nebraska City
    Crawford Home of Fort Robinson and site of key western events, this town's Pine Ridge landscape entertains visitors with activities like hiking, biking and golf. Crawford
    Valentine A cowboy spirit prevails in a town that's the base for canoe trips on the famed Niobrara River. Valentine
    Scottsbluff Get a taste of the Oregon Trail life at the namesake bluff, Chimney Rock and pioneer museums. Scottsbluff
    Ogallala Real-life cowboys hang out in a base for visitors to Lake McConaughy's white beaches. Ogallala

  • Ohio's old-fashioned charm

    Coshocton Living history abounds at Roscoe Village (left) with rides aboard horse-drawn boats on the Ohio-Erie Canal. Coshocton
    Berlin This Midwest Amish hot spot village has tours, crafts shops and home-style restaurants. Berlin
    Marietta You'll see lots of historic sites and old-time crafts in the area's first permanent settlement, along with boutiques and river cruises. Marietta
    Lebanon This antiquers' mecca is also home of the Golden Lamb Inn, which is more than 200 years old and once welcomed Charles Dickens. Lebanon
    Logan From here, you can explore the rolling woodlands of southern Ohio's Hocking Hills. Logan
    Cambridge You'll find glass factories, shops and museums, as well as Salt Fork State Park, Ohio's largest. Cambridge
    Granville Hilltop Denison University looks down on a New England-style town. Granville
    Yellow Springs Funky shops and cafes line the streets of this free-spirited college town near a 75-mile bike path. Yellow Springs
    Zoar A Utopian community lives on, with the help of reenactors. Zoar

  • South Dakota's Black Hills bounty

    Pierre Check out the state capitol and memorials, Lewis and Clark history and vast Lake Oahe. Pierre
    Custer City Growing like an Old West boom town, Custer City is the gateway to the Black Hills' best: Custer State Park, Mount Rushmore and Crazy Horse Memorial. Custer City
    Deadwood Its Old West aura is mostly intact despite a huge gambling scene. You'll also find lots of winter sports and stunning Black Hills scenery. Deadwood
    Hill City Another Black Hills boom in progress, this town has a growing group of art galleries as well as 1880s steam train rides. Hill City
    Hot Springs At the Black Hills' southern edge, Hot Springs has an important fossil dig and a wild horse sanctuary. Hot Springs

  • Wisconsin: Lakes, art and more

    Cedarburg This town's National Register limestone buildings are as sturdy as the work ethic of their German builders. Now they hold a wealth of shops and galleries. Cedarburg
    Lake Geneva Visitors can promenade like the Victorian socialites who founded this pretty resort town on the 21-mile path that winds around the lake, past grand estates. Lake Geneva
    Spring Green The inspired arts scene includes Frank Lloyd Wright's Taliesin home and studio and a world-class outdoor theater. The weirdly appealing House on the Rock is nearby. Spring Green
    Elkhart Lake A mix that surprisingly works: classic Victorian town with the four-diamond Osthoff resort and a road-race course with 400 annual events. Elkhart Lake
    Eagle River Summer is for lakeside resorts; winter is for snowmobiling on the extensive trail system. Eagle River
    Mineral Point Artists work among preserved buildings in an 1820s Cornish lead-mining town. Mineral Point
    Green Lake This is a quintessential Wisconsin lake town scene: water sports and supper clubs. Green Lake
    New Glarus You'll find a little bit of Switzerland, including Alpine architecture and Heidi and Wilhelm Tell weekends. New Glarus
    Ashland This town is home to Northern Great Lakes Visitor Center, ferries to the Apostle Islands and a serious ecoconscious ethic. Ashland
    Hudson Inns, antiquing and outdoor activities are popular in this pretty town in the St. Croix River Valley. Hudson
    Port Washington A lighthouse guards a Lake Michigan harbor that also has lakeside lodgings and dining. Port Washington
    Baraboo Location. Location. Location. It's near the Dells, Circus World Museum and 500-foot cliffs in Devil's Lake State Park. Baraboo
    Cambridge See Lake Ripley and the "Salt-glazed Pottery Capital of the World." Cambridge

    (A version of this story appeared in Midwest Living® May/June 2007. It was updated in April 2011.)

Add Your Comment