South Bend, Indiana: The University Town That Time Forgot
Just 95 miles from Chicago, South Bend is an underrated choice for a day trip from Chicago. While everyone knows about Notre Dame, few realize this college town offers way more than football tailgates. Notre Dame fans will enjoy checking out the campus and visiting the 125-year-old Basilica of the Sacred Heart. The Basilica is an incredibly impressive old church with gorgeous stained glass and high ceilings with large murals. The downtown area has undergone a major transformation, with craft breweries and farm-to-table restaurants popping up faster than you can say touchdown. Think of it as a mini Madison, Wisconsin – but without the tourist prices. Other South Bend activities include visiting the South Bend Chocolate Company, touring the Studebaker Museum, walking along the St. Joseph River, and seeing the flowers and succulents at Potawotami Conservatories.
Greenville, South Carolina: The Bridge to Everywhere
Having gone to high school in the downtown area of Greenville, our digital editor Kate McGregor says that a weekend here isn’t complete without a meal at Smoke on the River and a wander through the Main Street farmer’s market. Walk along the trails in the Reedy River Park for a spot of nature. This Southern gem sits perfectly between Atlanta and Charlotte, making it accessible for millions yet somehow remaining under the radar. The Liberty Bridge downtown is like Brooklyn Bridge’s cooler, less crowded cousin. What makes Greenville special isn’t just one thing – it’s the way everything flows together like the Reedy River that runs through its heart. The food scene here rivals Charleston, but you can actually get a table without a three-week wait. The craft beer scene is exploding, with local breweries serving up flavors as unique as the town itself.
Hudson Valley, New York: Antique Hunting Paradise
A quick trip from New York City or Connecticut, the Hudson Valley region of New York was made for design lovers and nature enthusiasts alike. Wander the picturesque towns to find handmade homewares and antique trinkets, and spend a fall Saturday hiking through the hills. This isn’t your typical weekend escape – it’s like stumbling into a Pinterest board that came to life. There are plenty of charming destinations to explore around the Hudson Valley—and many, including the city of Hudson, are reachable without a car. New Yorkers can hop on the Amtrak from Penn Station and check into Wm. Farmer and Sons along the Hudson River or The Maker, a cozy property known for its signature perfume collection and eclectic rooms filled with vintage finds. The rolling hills look like something straight out of a Thomas Kinkade painting, except real and way more Instagram-worthy. Apple picking in fall becomes a spiritual experience when you’re surrounded by mountains that seem to glow with autumn colors.
Burlington, Vermont: The Small City With Big Personality
Burlington, VT may not be on your radar as much as cities like New York or Philadelphia, but it’s small-town charm lends the perfect vibe for a weekend getaway. From live music and hip restaurants and shops to beautiful waterfront views of Lake Champlain (plus plenty of water activities and rentals during the summer months), Burlington has lots to keep you busy for the weekend without being overwhelming. This lakeside college town feels like what would happen if Portland, Oregon, and a Vermont maple farm had a baby. Best thing to do: Eat! Burlington is quickly becoming known as a foodie destination, with tons of unique and local restaurants, from food trucks to waterfront cafes to speakeasies and outdoor markets. The Church Street Marketplace buzzes with street performers and local artisans, while Lake Champlain provides a stunning backdrop that makes you forget you’re still on the East Coast. It’s the kind of place where craft beer flows like water and every restaurant seems to source ingredients from farms you can actually visit.
Salt Lake City, Utah: The Olympic City That’s Ready for You
The newly announced home to the 2036 Winter Olympics, Salt Lake City is an underrated long weekend getaway destination. Home to a vibrant art scene that includes Ballet West, The Utah Museum of Fine Arts, and the annual Sundance Film Festival, there’s plenty to see for all. Don’t let preconceptions fool you – this mountain city has transformed into one of America’s coolest urban destinations. The downtown area pulses with energy, craft breweries, and restaurants that would make any foodie weep tears of joy. You’re literally surrounded by mountains on all sides, making it feel like you’re in a natural amphitheater. The best part? You can ski world-class slopes in the morning and catch a symphony performance downtown the same evening. It’s like having Colorado’s outdoor playground with a surprisingly sophisticated cultural scene.
Cooperstown, New York: Beyond Baseball
Perched along the southern shore of crystal-clear Otsego Lake, Cooperstown is the type of place that inspires a day of aimless strolling with a coffee in hand. With just 2,000 locals as of 2023, the central New York village loves all things laid-back and cozy-but do not mistake sleepy for dull. While the small town may lack big-city attractions, this is half Cooperstown’s charm. Instead, it encourages visitors to ditch the go-go-go and embrace a relaxed stride. Yes, the Baseball Hall of Fame is here, but that’s just the opening act. This lakeside village feels like stepping into a Norman Rockwell painting where the coffee is actually good and the WiFi works. The Farmers’ Museum and Fenimore Art Museum offer surprises that make you question why you never heard about them before. Whether sitting in or ordering to-go, cafes are the perfect prelude to a day of exploring. It’s the kind of place where you plan to stay two hours and end up booking a room for the night.
New Haven, Connecticut: The Pizza Capital You Never Knew About
New Haven may be best known for being the home of Yale University but there’s plenty to explore in this charming cultural capital even without a coveted acceptance letter. From the restaurants and shops on Chapel St. to the delicious, dueling “apizza” joints, there’s more than enough to keep you busy for a full weekend. On top of that, almost all of the small city’s world-class museums are completely free. This Connecticut city invented American pizza as we know it – the thin-crust, coal-fired “apizza” that makes New York slices look like cafeteria food. After a multi-year renovation, the Yale Center for British Art recently reopened to once again welcome visitors to its fascinating exhibitions. Widely thought to have the greatest collection of British art outside of the UK, this must-visit institution is housed in a striking, brutalist Louis Kahn building that’s a work of art in itself. The combination of Ivy League sophistication and blue-collar pizza joints creates an atmosphere you won’t find anywhere else. Walking through the Yale campus feels like touring a movie set, while the surrounding neighborhoods offer authentic Italian-American culture that’s been simmering for over a century.
Livingston, Montana: Yellowstone’s Quieter Gateway
While many choose the city of Bozeman as a base camp to explore the wonders of Yellowstone National Park, Livingston is a vastly underrated alternative. “The Gateway City,” as many call it, is about an hour’s drive from the park; however, it served as Yellowstone’s original rail entrance. Today, the historic rail town stands apart from Bozeman due to its rich history and quaintness, inviting Yellowstone adventurers to embrace a slower pace. This former railroad town sits in the Paradise Valley with mountain views that make you understand why Montana is called Big Sky Country. Surrounded by pockets of Gallatin National Forest, Livingston also offers its own natural attractions. For a night under the stars, the Pine Creek Campground provides seclusion and scenic forest scenes. The campground is also close to the Pine Creek Falls Trailhead, a challenging hike with an enchanting finale: a spellbinding 100-foot waterfall. The downtown historic district feels like stepping back in time, but with craft breweries and farm-to-table restaurants that remind you you’re still in the 21st century. It’s what Jackson Hole was like before it became a playground for millionaires.
Annapolis, Maryland: Sailing Into History
Annapolis, Maryland is a charming coastal city situated about 45 minutes from Washington D.C. It can make for a delightful weekend getaway filled with history, maritime culture and scenic beauty. This picturesque town, home to the United States Naval Academy, invites visitors to explore its colonial-era streets lined with historic homes, cozy cafes and boutique shops. This waterfront city combines the gravitas of being Maryland’s capital with the laid-back vibe of a sailing town. Visitors can take a guided tour of the Naval Academy, marvel at the impressive sailing vessels docked at the City Dock or indulge in fresh seafood at one of the waterfront restaurants. The Annapolis Maritime Museum and the Maryland State House, the oldest state capital in continuous legislative use, provide a glimpse into the city’s rich heritage. Every summer weekend, the harbor fills with sailboats that look like they sailed straight out of a Ralph Lauren ad. The cobblestone streets and 18th-century architecture make you feel like you’re walking through American history, while the waterfront restaurants serve up blue crabs that’ll make you forget Baltimore exists.
Rehoboth Beach, Delaware: The Nation’s Summer Capital You Can Afford
Rehoboth Beach, Delaware, a charming coastal town located about a 2.5-hour drive from DC, offers a delightful weekend getaway filled with sun, sand and seaside charm. This vibrant beach community boasts a mile-long boardwalk lined with eclectic shops, restaurants and amusement park rides. It’s a perfect destination for families and beachgoers alike. Visitors can spend their days in the sun on the sandy shores, indulging in fresh seafood at one of the local eateries or exploring the quaint downtown area with its colorful boutiques and art galleries. What sets Rehoboth apart from other East Coast beach towns is its authentic, unpretentious vibe – think Ocean City without the spring break chaos. The town has attracted everyone from Joe Biden to countless Washington power players, but it never lost its small-town beach charm. The boardwalk feels like a throwback to simpler times, when a funnel cake and some arcade games could make your whole weekend. Plus, Delaware’s tax-free shopping means your beach vacation doubles as a retail therapy session.
Bear Mountain, New York: Nature’s Quick Escape
In the time it would take to make it across town during rush hour, adventurers can get to Bear Mountain for an easy escape from city madness. The state park, situated in the mountains rising from the west bank of the Hudson River, which offers a bevy of hiking and biking trails, as well as picnic groves, lake and river fishing access, a swimming pool and a zoo. This isn’t just a park – it’s proof that you don’t need to drive to Vermont to feel like you’ve escaped civilization. Bear Mountain Inn, originally built in 1915, hosted Eleanor Roosevelt, Harry Truman and Dwight Eisenhower back in the day, and has been extensively renovated to include 15 luxury guest rooms, plus a spa and a restaurant. The hiking trails range from gentle lakeside strolls to challenging mountain climbs that reward you with views stretching across three states. What makes this place special is how quickly the city noise fades into bird songs and rustling leaves. It’s like having the Adirondacks in your backyard, complete with a historic lodge that makes you feel like you’re staying at a national park without the crowds.
Old Saybrook, Connecticut: Katharine Hepburn’s Secret Paradise
The former summer home of Katharine Hepburn, the acclaimed actress once used Old Saybrook as a weekend escape for a break from the hustle of everyday life. Today, Old Saybrook remains a spirited summer destination, inviting guests to experience “Katharine Hepburn’s Paradise” at locales like Harveys Beach and the Katharine Hepburn Cultural Arts Center. This Connecticut shoreline town offers the kind of New England coastal experience that makes you understand why Hollywood royalty chose it as their retreat. On June 22nd, 2025, the town will also host its third annual Celebrate Saybrook Street Party on Main Street. Locals and out-of-towners alike are invited to enjoy vendors, live music, and great food from merchants like Vecchitto’s Italian Ice and Los Mariachis on Wheels. Many of Main Street’s usual boutiques and shops will also partake in the festivities, including Maximus Antiques and Smartyplants Design. The beaches here feel private even when they’re not, and the town center maintains that classic New England charm without the Hamptons price tag. It’s where Connecticut locals go to avoid the Connecticut tourists, if that makes sense.
Whittier, Alaska: The Strangest Small Town in America
While Anchorage, Juneau, and Fairbanks are Alaska’s largest and most well-known cities, small towns like Whittier are just as enchanting. This might be the most unusual weekend getaway in America – a town where nearly everyone lives in the same building and you can only reach it by tunnel or boat. Whittier sits at the head of Prince William Sound, surrounded by glaciers and waterfalls that make Swiss Alpine postcards look ordinary. The whole town feels like a social experiment that worked out better than anyone expected. You can watch whales from your hotel window, take glacier cruises that last all day, and experience the midnight sun in summer or the aurora borealis in winter. It’s not just remote – it’s otherworldly, like staying in a research station at the edge of the world, except with surprisingly good seafood and the friendliest neighbors you’ve ever had.
What makes these places special isn’t just their proximity to major cities or their Instagram-worthy views. It’s that they offer something increasingly rare in our hyper-connected world: the chance to discover a place that hasn’t been completely discovered yet. Each destination tells its own story, whether it’s through the cobblestones of Annapolis or the railroad history of Livingston. They’re proof that the best weekend getaways aren’t always the ones everyone’s talking about – sometimes they’re the ones quietly waiting for you to find them.
