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Memorial Day Weekend has a way of sneaking up fast. Still, thankfully, some of the best long-weekend escapes are surprisingly close to home—especially for travelers based near major cities like New York City, Boston, Chicago, San Francisco and Orlando. Within just a short drive, it’s easy to swap city life for beach days, lake weekends, mountain air or vineyard views without wasting half the holiday in transit.
From historic coastal towns to outdoorsy lake escapes and wine-country retreats, these Memorial Day weekend getaways are ideal for travelers looking to maximize the unofficial start of summer with minimal planning and maximum sunshine.
Napa Valley, CA
Nearest major city: San Francisco (63 miles, or 1 hour and 30 minutes)
The world-renowned Napa Valley makes for an easy wine country escape—especially during the summer months, when vineyard views, outdoor tastings and warm-weather dining are at their best. It’s also an especially exciting time to visit, thanks to the reopening of the iconic Robert Mondavi Winery after a years-long renovation. Of course, wineries abound throughout the region, including Sterling Vineyards, the only winery in the world accessible by gondola, with sweeping valley views and self-guided hilltop tastings. And for travelers looking to sit back and enjoy the scenery between tastings, the Napa Valley Wine Train offers multi-course dining journeys and vineyard tours through the heart of wine country.
Where to stay: In the charming town of Yountville, Hotel Villagio at the Estate Yountville offers resort-style amenities—including a pool, landscaped grounds and a swanky spa set to reopen later this summer—while still maintaining a boutique feel. The property is also home to the Instagram-worthy Clementine restaurant, and it’s just steps from some of Napa’s most acclaimed eateries, including Thomas Keller hotspots like the French Laundry and Bouchon.
The Poconos, PA
Nearest major city: New York (95 miles, or 1 hour and 45 minutes)
An easy drive from New York City, the Poconos is an outdoor escape known for its forested mountains, cascading waterfalls and clear lakes, which means adventure opps abound. Travelers can hike through spots like Bushkill Falls—known as the “Niagara of Pennsylvania”—and the Delaware Water Gap, or kayak or boat along Lake Wallenpaupack, which boasts over 50 miles of shoreline. There’s also Lehigh Gorge State Park, known for its scenic trails, waterfalls, and biking paths that run alongside the river. The region is also dotted with charming small towns like Jim Thorpe—also known as the “Switzerland of America” for its architecture and picturesque setting—along with Milford and Stroudsburg, both filled with local cafés, galleries and historic main streets.
Where to stay: The best place to stay in the Poconos depends on your travel style and who you’re traveling with. For an adults-only escape, check into the Lodge at Woodloch, an all-inclusive wellness oasis known for its nature-focused programming, guided outdoor activities and sprawling spa complete with hydrotherapy pools, saunas and even a snow room (which, yes, is really a chilly room covered in snow). Families, meanwhile, will love sister property the Pines at Woodloch, a sprawling all-inclusive resort set on more than 1,200 acres with lakeside activities, nightly entertainment, pools, boating and a laid-back, summer-camp-like atmosphere.
The Berkshires, MA
Nearest major city: Boston (125 miles, or 2 hours)
I could write ad nauseam about the Berkshires at any time of year, but early summer is by far my favorite time to visit this corner of western Massachusetts, just before the peak summer crowds fully arrive. The region feels especially idyllic that time of year, with rolling green hills, farm stands and warm, sunny weather for hiking and boating. What makes the Berkshires especially fun to explore is that each town—from rustic-leaning Pittsfield to artier enclaves like Lenox and Great Barrington—has its own distinct personality despite being just a short drive from one another. Add in stops like Mass MoCA, Norman Rockwell Museum, Tanglewood, the Mount, Mount Greylock, local bookstores and roadside farm stands, and you’ve got a solid weekend escape.
Where to stay: While many Berkshires stays lean rustic and outdoorsy, 33 Main – An Annie Selke Luxury Lodging Experience offers something far more contemporary and polished. Helmed by Lenox native and celebrated designer Annie Selke, the boutique property feels as if it were pulled straight from the pages of an interior design magazine, with layered textiles, bright, modern interiors and cozy common spaces.
Lake Geneva, WI
Nearest major city: Chicago (125 miles or 2 hours)
Situated along the shores of southeastern Wisconsin, Lake Geneva is far more than a quaint lake town. A stroll along the scenic Shore Path reveals sprawling Gilded Age mansions that rival those in Newport, including architectural landmarks like the 19th-century Black Point Estate & Gardens, once built as lavish summer homes for wealthy Chicago families. Memorial Day weekend is an especially ideal time to visit, when the town fully shifts into summer mode with boating and beach days at hotspots like Big Foot Beach State Park, which also offers picnic areas, swimming spots and more than five miles of hiking trails overlooking the lake. Beyond the water, visitors can go ziplining at Lake Geneva Ziplines & Adventures, visit Safari Lake Geneva or spend the afternoon sipping libations at Geneva’s first and only winery and distillery, aptly named Geneva Lake Distilling + Winery.
Where to stay: Set on 1,300 acres just outside downtown Lake Geneva, Grand Geneva Resort & Spa offers something for nearly every type of traveler, from championship golf courses and a large spa to horseback riding, hiking trails and outdoor pools. Families will also appreciate Timber Ridge Lodge & Waterpark, located on the resort grounds, with indoor and outdoor water attractions that make it especially appealing for Memorial Day weekend and summer trips with kids.
St. Augustine, FL
Nearest major city: Jacksonville (41 miles, or 45 minutes), Orlando (104 miles, or 1 hour and 45 minutes), Tampa (180 miles, or 2 hours)
What better place to spend Memorial Day weekend than America’s oldest city? Founded in 1565, St. Augustine blends centuries of history with laid-back beach-town energy, where Spanish colonial architecture, cobblestone streets and waterfront views all collide in one compact, walkable destination. Travelers can explore landmarks like Castillo de San Marcos and Flagler College, browse the boutiques and restaurants lining pedestrian-only St. George Street or lean into the city’s famously haunted reputation with one of its many ghost tours after dark. Like many other places in the country, Memorial Day weekend also marks the unofficial start of beach season here, with nearby stretches of sand like Anastasia State Park drawing visitors for swimming, boating and long days by the Atlantic.
Where to stay: The upscale Casa Monica Resort & Spa, Autograph Collection stands out for its striking Moorish Revival architecture, Old World–inspired interiors and accommodations that feel far more timeless and romantic than sleek or contemporary. There’s also a museum-worthy curated art collection, rooftop pool deck and lively lobby bar, which is prime for people-watching.