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

Editor’s Note: NEA Member Benefits understands how much you love to travel and how much you’ve missed it. As states begin to relax their regulations with regard to COVID-19 and more Americans become vaccinated, travel is opening up more and more. Before planning a trip, read the health and safety protocols and requirements for visitors to any destination, as well as those of airlines, car rentals and hotels before booking and again before traveling.

Weekend getaways are an art—a tried-and-true American pastime. They’re a mainstay for travelers who can’t plan longer trips for one reason or another because it’s easy to go somewhere fun and new without spending a lot of money. 

While larger cities such as Chicago and Miami often get the most attention, the U.S. is full of charming smaller cities that are worthy of exploration. Places such as Portland, Maine; Asheville, North Carolina; and Louisville, Kentucky, all offer amazing food, stunning scenery, diverse cultures 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 was 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 affordable motels and chains including Hampton Inn and Red Roof, as well as family-friendly hotels with spacious rooms at a steal. 

So pack your bags and spend your next long weekend getaway in one of these unexpectedly interesting small cities. And, when you reserve your trip, don't forget about money-saving deals on hotel bookings, car rentals and airfare through NEA Travel.

Portland, Maine

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

Photo courtesy of Corey Templeton Photography

Often confused with the other Portland (the one in Oregon), this smaller city, which is 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).

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, which includes a 2-mile-long harborside promenade among its 68 acres that were designed by the Olmsted Brothers in 1905 (yes, the same landscaping firm that designed Central Park in New York).

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 also can 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 such as Andy Warhol and Claude Monet, its focus is on art from the region. And the outdoor David E. Shaw and Family Sculpture Park is great fun for families. The museum is free every Friday from 4–8 p.m.

To splurge on dinner, head to Eventide Oyster Co., Central Provisions, The Honey Paw, Scales or Fore Street. Budget-friendly options include Duckfat, Crispy Gai, Salvage BBQ and Palace Diner (Maine’s oldest diner, in nearby Biddeford). For a classic deli breakfast, be sure to hit up Rose Foods. Belleville will satisfy your pastry cravings.

NEA member travel benefits: Fly into Portland International Jetport (PWM); NEA Travel: Flights is the best place to find great prices on airline tickets. Then on the hotels page you can find prices including an average of $215/night at the Best Western Merry Manor Inn, which has a heated outdoor mineral pool, an indoor whirlpool with waterfall and a children’s pool, plus some rooms with fireplaces. For a real adventure, book a room at the Inn at Diamond Cove (average of $159/night), which is on an island in Casco Bay, a short ferry ride away from Portland’s Old Port District. Set inside an old fort from the 1890s, the hotel has everything from a pool to tennis courts to duckpin bowling, plus a waterfront restaurant with local seafood.

Plan your itinerary: Visit Portland Maine | Visit Maine

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.

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

For shopping and entertainment, visit Downtown’s Fourth Street Live! It's a 350,000-square-foot complex with 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.

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—find it at the Brown Hotel or Bristol Bar & Grille. Also save room for biscuits and gravy at Biscuit Belly, amazing Mexican food at Mayan Café, and farm-to-table New American cuisine at Decca. For a splurge, make reservations at famous chef Edward Lee’s 610 Magnolia or Proof on Main at the 21c Museum Hotel where the art is as impressive as the food. For food and a drink, head to Copper & Kings distillery where you can tour the facility and dine on small plates or brunch at the rooftop restaurant.

NEA member travel benefits: For a great deal, book a flight through NEA Travel: Flights to Louisville Muhammad Ali International Airport (SDF). The hotels booking page features deals including an average of $189 a night at the historic Galt House Hotel Trademark Collection by Wyndham or $195 for the legendary Brown Hotel, which was built in 1923 in the Georgian Revival style and is credited with inventing the Hot Brown sandwich. For something more modern, there’s the Moxy Louisville Downtown, for an average of $199 a night.

Plan your itinerary: Louisville Tourism | Kentucky Tourism

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. From the top of the dunes, you can see right across Lake Michigan. 

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

NEA member travel benefits: Buy airfare tickets for Cherry Capital Traverse City Airport (TVC) through NEA Travel: Flights for great prices. Next, look for hotels on the NEA Travel: Hotels page. There, you’ll see deals including an average of $174 per night (including daily breakfast) at the waterfront Victorian style Bayshore Resort and $165 per night for Best Western Plus Traverse City. If you’re traveling with kids, consider a room at Great Wolf Lodge Traverse City, for an average of $141 per night, because it has a gigantic indoor waterpark inside the hotel.

Plan your itinerary: Traverse City Tourism | Pure Michigan

Asheville, North Carolina

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

Photo courtesy of

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—you can listen to buskers in many city plazas or get tickets to a show at the famous Orange Peel music venue. The city is also an art-and-craft hub with makers found on every street.

Architecture lovers will enjoy the well-preserved Art Deco buildings and the massive Vanderbilt estate called Biltmore. The 175,000-square-foot home was built in the late 1890s on a then-125,000-acre plot, with the original landscape plan devised by Frederick Law Olmsted. Biltmore hosts seasonal activities from a springtime garden show to special tours of the estate’s lavish Christmas decorations during the holiday season. Reserve at least half a day for Biltmore, which in addition to the main house has extensive gardens, shops, restaurants and its own functioning winery.

Visitors should make sure to explore the lively River Arts District, which boasts restaurants and open artist studios; hike and bike the Pisgah National Forest; get your game on at the well-stocked Asheville Pinball Museum; and see the wildlife at the Western North Carolina Nature Center. Between Thanksgiving and New Year’s Day, plan a visit to the Omni Grove Park Inn to marvel at all of the spectacular entries in the National Gingerbread House Competition.

Save your appetite for the city’s impressive food scene—try beloved local chef Katie Button’s Spanish tapas restaurant Curate, farm-to-table spots such as Rhubarb and the Market Place, Appalachian cuisine at Haywood Common, and famous barbecue spot Buxton Hall. And if you don’t eat gluten, check out Posana, whose kitchen is entirely gluten free. Sample sweets at French Broad Chocolates, or head to the one-of-a-kind Hole Doughnuts. You may have to wait a bit to get your hands on this doughy goodness, but we promise you it's worth it.

NEA member travel benefits: Book a flight through NEA Travel: Flights to Asheville Regional Airport (AVL) to get great airfare prices. You might find more flight options by flying into Greenville-Spartanburg International Airport (GSP), which is about 75 miles south. Visit NEA Travel: Hotels to find deals at hotels including an average of $137 a night at the excellently located Four Points by Sheraton Asheville Downtown, $158 a night at the art-forward Hotel Indigo Asheville Downtown, an IHG Hotel, and $215 a night for the historic Haywood Park Hotel, an Ascend Hotel Collection, which is inside an old Art Deco department store.

Plan your itinerary: Explore Asheville | Visit NC

Santa Barbara, California

Best Cities for Long Weekends - Santa Barbara, California

Two hours north of Los Angeles, you’ll find 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, biking around the Funk Zone and exploring the downtown Urban Wine Trail are just a few of the city’s attractions.

Also worth a visit is 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, get a pizza (or two) 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 the Lark. And, of course, save room for a scoop or two of McConnell’s Fine Ice Creams, which was founded here, and pastries and other treats from Helena Avenue Bakery.

NEA member travel benefits: Book a flight through the NEA Travel Program to Santa Barbara Airport (SBA), Bob Hope Burbank International Airport (BUR) or Los Angeles International Airport (LAX), which is about 80 miles away. Visit NEA Travel: Hotels to find deals at hotels such as Hotel Santa Barbara, right downtown, for an average of $204/night, and Hotel Milo, across the street from the beach and with two pools and free bike rentals, for an average of $206/night. If you’re looking to earn Hilton Honors loyalty points, the Hilton Santa Barbara Beachfront Resort features classic Spanish colonial architecture and has a pool, tennis and basketball courts and a full-service spa, for an average of $243 a night.

Plan your itinerary: Visit Santa Barbara | Visit California

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