America’s Best Small Cities for a Long Weekend

Long holiday weekend on the horizon? Head for one of these small but exciting U.S. cities that you can explore in just a few days.

Couple Dining Out in Asheville, NC

by NEA Member Benefits

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Weekend getaways are an art—a tried-and-true American pastime. A mainstay for travelers that can’t plan longer trips for one reason or another, it’s easy to go somewhere fun and new without spending a lot of money. While larger cities like Chicago and Miami often get the most attention, the U.S. is full of incredibly interesting smaller cities that are more than worth exploring. Places like Portland, Maine; Asheville, North Carolina; and Louisville, Kentucky, all offer amazing food, beautiful scenery, unique culture and plenty of local shopping. Best of all, you can usually see most of the highlights and a few lesser-known gems over a long weekend.

Each of these cities were selected because of the range of activities offered as well as the destination’s affordability. While you’ll find top-end full-service hotels and boutique lodgings in each city, you’ll also find plenty of family-friendly motels and chains like Hampton Inn and Red Roof. So pack your bags and spend your next weekend getaway in one of these exciting small cities. And, when you reserve your trip, don't forget about money-saving options such as hotel bookings through NEA Vacations, a 20% discount at Red Roof locations and a break on car rentals from Enterprise, Hertz, Alamo, Dollar and National.

Portland, Maine

Best Cities for Long Weekends - Boats Docked in Portland, ME

Photo courtesy of Corey Templeton Photography

Often confused with the other Portland, this smaller city, that’s about a two-hour drive from Boston, has about as much to offer in the way of food as the West Coast city of the same name. But, the food here is infused with the spirit of New England. In between bites of freshly caught lobster (try the Highroller Lobster Co. or Portland Lobster Co.), explore historic lighthouses. Pick from Portland Head Light, built in 1791; the 1875 Bug Light and Portland Breakwater Light (1855). Each is an ideal spot for selfies.

There are also two parks in the area that are especially appealing: Fort Williams Park, which is 90 acres of nature with an arboretum, small beach, children’s garden and gun batteries to enjoy; and Eastern Promenade, that puts on free evening concerts in the summertime.

If you want to step into a quintessential New England fishing village, head to downtown’s Old Port District, with its cobblestone streets, historic buildings and cute places to window shop.

Families can also do the self-guided Portland Freedom Trail, which has 16 marked historic sites that played a role in Portland’s abolitionist movement and Underground Railroad, including homes, churches and buildings with hidden passageways.

For art lovers, there are plenty of galleries downtown to visit, and the Portland Museum of Art never disappoints. While it offers a range of works from artists like Andy Warhol and Claude Monet, its focus is on art from the region. And, May through December, the outdoor David E. Shaw and Family Sculpture Park is great fun for families. The museum is free on the first Thursday of each month from 5–8 p.m.

To splurge on dinner, head to Eventide Oyster Co., Central Provisions or Fore Street. Budget-friendly options include Duckfat, Salvage BBQ and Palace Diner.

Planning a visit: Visit Portland Maine | Visit Maine

Driving distances: 1 hour 30 mins from Manchester, New Hampshire | 2 hours from Boston, Massachusetts | 3 hours from Providence, Rhode Island, and Hartford, Connecticut | 4 hours from Albany, New York

Where to stay: Hilton Garden Inn Portland Downtown Waterfront | Ramada Plaza by Wyndham Portland | Motel 6 Portland ME

Louisville, Kentucky

Best Cities for Long Weekends - Fourth Street Live in Louisville, KY

Photo courtesy of Louisville Tourism

Horse lovers, sports fanatics, music fans and food connoisseurs alike will all fall in love with Louisville. It’s a small urban city but with the Old Louisville district, you can still stroll along a street shaded by old-growth trees as you spy Victorian-era homes.

Hugging the Ohio River, the city has lovely views, plenty of green space and historic homes and buildings.

Churchill Downs, the home of the Kentucky Derby, is a must-visit—even if there’s no horse race, there’s a great museum. Also check out the Louisville Slugger Museum & Factory; Louisville Mega Cavern, where you can zip line underground; and the Muhammad Ali Center, the boxer was born in Louisville.

For shopping and entertainment, visit Downtown’s Fourth Street Live! It's a 350,000-square-foot complex on 4th Street between Muhammad Ali Blvd. and Liberty. There’s fast-food, sit-down restaurants, nightclubs and more to keep you busy.

For some outdoor time, visit the Parklands of Floyds Fork, where you can bike, paddle, fish and enjoy playgrounds and water spray areas. Get some bragging rights by walking across the Big Four Bridge to Indiana, or treat the family to a day at Kentucky Kingdom, the city’s amusement park. You can even walk across the Big Four Bridge to Indiana.

While you’re in town, you must try the city’s famous open-faced sandwich, a Hot Brown. It features turkey, bacon and a creamy Mornay sauce. Also save room for biscuits and gravy at Biscuit Belly, amazing Mexican food at Mayan Café, Italian-inspired cuisine at Impellizzeri’s Pizza and enjoy locally sourced ingredients in German-American dishes at Eiderdown.

Planning a visit: Louisville Tourism | Kentucky Tourism

Driving distances: 1 hour 30 mins from Cincinnati, Ohio | 2 hours from Indianapolis, Indiana | 3 hours 30 mins from Nashville, Tennessee; Charleston, West Virginia; and Columbus, Ohio | 4 hours from St. Louis, Missouri

Where to stay: Red Roof Louisville Fair and Expo (Don’t forget to use your member benefits!) | Homewood Suites by Hilton Louisville Downtown | Holiday Inn Express & Suites Louisville Downtown

Traverse City, Michigan

Best Cities for Long Weekends - Sleeping Bear Dunes National Lakeshore, Traverse City, Michigan

The “Cherry Capital of the World,” Traverse City is a beautiful town set on the shores of Lake Michigan. The picturesque downtown is perfect for strolling, with stops at boutiques, restaurants, coffee shops and galleries along the way. You’ll also want to eyeball the impressive City Opera House, which dates back to 1891. Rent bikes to explore Clinch Park or the city’s extensive paved TART trail network.

While there’s a lot to do in Traverse City itself, don’t neglect the lake—it’s perfect for lolling on the beach, kayaking or swimming. Or, drive 28 miles to see the stunning—and climbable—dunes at Sleeping Bear Dunes National Lakeshore. Once you’re at the top of the dunes, you can see right across Lake Michigan. 

Get your cherry fill at one of the dozens of stands around the lake each summer, sample delectables such as cherry jam and cherry cream soda at Cherry Republic, or get your fill of cherry pie at the Grand Traverse Pie Company.

Planning a visit: Traverse City Tourism | Pure Michigan

Driving distances: 2 hours from Grand Rapids, Michigan | 4 hour 30 mins from Detroit, Michigan, and Toledo, Ohio | 5 hours from Chicago, Illinois and Fort Wayne, Indiana

Where to stay: Great Wolf Lodge Traverse City | Comfort Inn Traverse City | Hampton Inn Traverse City | Courtyard Traverse City

Asheville, North Carolina

Best Cities for Long Weekends - Happy Couple Dining Out in Asheville, NC

Photo courtesy of ExploreAsheville.com

This charming mountain city is perched amid the Blue Ridge Mountains, making nature easily accessible. It’s also the center of North Carolina’s bluegrass culture—stop to hear buskers in many city plazas or get tickets to a show at the Orange Peel. Architecture lovers will enjoy the well-preserved Art Deco buildings and the massive Vanderbilt estate called Biltmore, which also hosts seasonal activities like a springtime garden show and special tours of the estates Christmas decorations during the holiday season. The city itself is an art and craft hub with makers found on every street.

Reserve at least half-a-day for Biltmore, which in addition to the main house has extensive gardens as well as its own functioning winery.

Visitors should make sure to explore the lively River Arts District, which boasts restaurants and artist studios; hike and bike the Pisgah National Forest; launch balls at the well-stocked Asheville Pinball Museum; and see the wildlife at the Western North Carolina Nature Center.

Save your appetite for the city’s impressive food scene—try one of chef Katie Button’s multiple restaurants such as Curate or Button & Co. Bagels, farm-to-table spots like Rhubarb and the Blackbird, and famous barbecue spot Buxton Hall. Finally, don't miss the one-of-a-kind Hole Doughnut. You may have to wait a bit to get your hands on this doughy goodness but we promise you it's worth it.

Planning a visit: Explore Asheville | Visit NC

Driving distances: 2 hours from Knoxville, Tennessee | 2 hour 30 mins from Charlotte, North Carolina | 3 hours from Columbia, South Carolina | 4 hours from Atlanta, Georgia and Roanoke, Virginia | 5 hours from Nashville, Tennessee

Where to stay: Quality Inn Asheville Downtown Tunnel Road | Days Inn by Wyndham Asheville Downtown North | Country Inn & Suites by Radisson, Asheville West, NC

Santa Barbara, California

Best Cities for Long Weekends - Santa Barbara, California

Two hours north of Los Angeles lies this oceanfront paradise, complete with dramatic cliffs and wide beaches—there’s a reason it’s called the American Riviera. Gorgeous cliff walks, beach time, whale watching sailing excursions and the downtown urban wine trail are just a few of the city’s attractions.

Also worth a visit is the new MOXI, The Wolf Museum of Exploration + Innovation. This science museum blends STEM with the arts to forge a more compelling experience for people of all ages. The historic and beautiful 18th-century Mission Santa Barbara and gardens is popular for weekend visitors as is the bustling Stearns Wharf, the Santa Barbara Museum of Natural History Sea Center and El Presidio Real de Santa Barbara, a fortified military settlement founded by the Spaniards in 1782.

When hunger hits, try get pizza at Bettina (owned by two Brooklyn expats), try tacos at La Super-Rica Taqueria (a favorite of Julia Child), indulge in Indian food at Bibi Ji or coastal cuisine at Barbareño. And, of course, save room for a scoop or two of McConnell’s Fine Ice Creams, which was founded here.

Planning a visit: Visit Santa Barbara | Visit California

Driving distances: 2 hours from Los Angeles, California | 2 hours 30 mins from Bakersfield, California | 4 hours 30 mins from San Diego, California | 5 hours 30 mins from Las Vegas, Nevada and San Francisco, California

Where to stay: Ramada by Wyndham Santa Barbara | Quality Inn Santa Barbara | Agave Inn

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