It’s wild to think of how quickly summer flies by every year. Yet while the summer travel season starts to wind down and we wonder where the summer went, we still have Labor Day Weekend to plan one more exciting and refreshing summer trip. We know that making summer vacation plans isn’t everyone’s cup of tea, so we’re going out of our way to point out the destinations where you can escape the most maddening Labor Day weekend crowds without completely breaking the bank.
- Wait, summer’s almost over?
- Portland, Maine
- Newport, Rhode Island
- Harpers Ferry, West Virginia
- The Delaware coast
- Savannah, Georgia
- Yellow Springs, Ohio
- Lake Geneva, Wisconsin
- St. George, Utah
- Whidbey and Camano Islands, Washington
- San Luis Obispo, California
- Looking for more ideas?
- Before we go, a few more thoughts
Now that summer is about to come to a close, here are some great ideas on where you can go to enjoy one last gasp of summer warmth. Here’s your last chance to discover your new favorite beaches, explore some great outdoor markets, sport your warm-weather hiking attire, find your perfect spot on the lake, and simply soak up the extra hours of sunshine.
Perhaps time really does fly by while we’re having fun. We just get finished talking about trips like the ones on our list of all-American destinations for the Fourth of July, and the back-to-school ads start popping up signaling we only have so many more dog days of summer left to savor.
While some parts of the U.S. enjoy pleasantly warm weather well into the fall, the rest of America may not have much longer before they have to break out their fall/winter clothing and turn on their heaters. With that said, we want to highlight a few special destinations across the nation where you can enjoy one more summer trip. Whether you’re more in the mood for a leisurely road trip or a fast weekend flight, here are our suggestions for a Labor Day weekend trip that won’t cause you too much undue labor.
If you’d like to escape to the New England coast, you might want to ditch the massive crowds at Cape Cod and come up to Portland, Maine, instead. In Portland, you have easy access to some of New England’s finest beaches, including Scarborough and Old Orchard Beach. If you prefer to stay in town, Portland has a very vibrant arts scene, a thriving foodie scene, and bursts of creativity all over Downtown. While Portland feels far removed from the hustle and bustle of the big cities, it’s only a 100-mile drive from Boston, and Portland has Amtrak train service and a full-service airport.
If you want to stay at the center of the action, try the Canopy by Hilton for their chic Luna Rooftop Bar and a convenient location near Portland’s iconic working harbor. Fortunately, late summer is a great time to enjoy some world-famous Maine lobster, and you can always swing by local favorites like DiMillo’s and Highroller Lobster for the freshest seafood you might find anywhere.
While your aspiring influencer friends are flexing like crazy in The Hamptons, you can hang with the “if you know, you know” jet set in Newport. Situated a mere 80 miles south of the city of Boston and 180 miles northeast of New York City, Newport offers a more relaxed yet very luxurious atmosphere with a plethora of historic mansions, scenic beaches, sailing boats, and much more. If you want some quality time at the beach, not only does Fort Adams State Park offer scenic harbor views and a mellow shoreline, but it’s also chock full of early American history. If you’re more in the mood for surfing and boogie boarding, Easton’s Beach (or First Beach) offers better waves and a wider stretch of sand.
If you’re in the mood to get away from it all, you’ll likely enjoy the calm yet sophisticated atmosphere of Castle Hill Inn near Fort Adams. With 40 acres of beautifully manicured grounds, two delectable restaurants, and easy access to private beaches, this might be your new favorite coastal home away from home.
In October 1859, John Brown led a rebel party to Harpers Ferry to free the local slave population and wage a bloody battle against those who enforced this heinous form of institutionalized racism. From there all the way to Confederate General Jubal Early’s 1864 (failed) attempt to blaze through Harper’s Ferry in order to attack Washington, Harpers Ferry played a critical role throughout the Civil War. History buffs and nature lovers will love Harpers Ferry National Historical Park for its stunning Appalachian scenery and its rich historical prominence.
These days, Harpers Ferry is also known and loved as a convenient getaway for Washingtonians seeking some solace from whatever’s trending on Capitol Hill. If a mountain retreat sounds more like your jam, the area offers a wide array of campsites, vacation rental cabins, and additional lodging options. If you’re looking for good dining options in town, you probably can’t go wrong at The Rabbit Hole Gastropub (with a robust selection of craft beers) and Kelley Farm Kitchen (with unbelievably yummy vegan food).
Who said New England gets to have all the aquatic fun? If you want a Mid-Atlantic beach retreat without the gnarly traffic of the Jersey Shore or Virginia Beach, try Delaware instead. With multiple beautiful beach towns — including Rehoboth Beach, Bethany Beach, and Fenwick Island — to explore, there’s never a dull moment here. At the same time, it’s incredibly easy to find the perfect beach along the Delaware coastline to sit back, relax, jump in the water, and let all your worries sail away. And if you’re looking for an LGBTQ+ friendly beach town, Rehoboth Beach has recently emerged as a laid-back Mid-Atlantic alternative to the more hectic crowds in Provincetown.
If you want to stay at a great hotel that’s right on the beach, it’s hard to beat the Boardwalk Plaza Hotel in Rehoboth. And if you love seafood, you will probably have a fabulous dinner at Henlopen City Oyster House, where you can feast on oyster shooters, lobster mac and cheese, and plenty more edible delights made with sustainable seafood.
Heading on down to the steamy South, we land in Savannah. While the city of Atlanta has gradually become Georgia’s most famous city thanks to its economic powerhouse status and celebrity star power, Savannah offers a different side of the Peach State, as well as its own unique charm thanks to its rich historical tapestry, its unique culinary scene, and its eclectically fun style. You can start your Savannah adventure at its famed City Market — where you can find galleries featuring emerging local artists and many of the region’s hottest restaurants — and go on to explore the city’s iconic pocket park squares, its centuries-old architecture, and the cool beaches of Tybee Island.
If you want to taste for yourself why Savannah’s restaurant scene has such an outsized influence over American dining, you probably want to try Repeal 33 and The Grey. If you want a spooky yet swanky place to hang your hat, The Marshall House and Kehoe House are famous for their “haunted house” atmosphere and their many luxurious amenities.
While it may seem quite off the beaten path, Yellow Springs has cultivated a reputation of beating to its own drum. Yet since it’s only about 60 miles from Columbus and Cincinnati, this western Ohio town is surprisingly approachable. Whether you’re into sampling sophisticated wineries, hunting down rare vintage comic books, tasting locally brewed beers, or wandering through the many more eclectic shops that define the downtown area, you can find plenty to do in Yellow Springs. Even better, Glen Helen Nature Preserve and Clifton Gorge Nature Preserve offer prime hiking and biking opportunities outside.
If you’re hungry after a long day of hiking and/or perusing, stop at the Historic Clifton Mill Restaurant for good ol’ home-cooked deliciousness in a historic setting, as well as Calypso Grill for some surprisingly good Caribbean-inspired fare. For a cozy yet sophisticated inn, try the Mills Park Hotel for a convenient location and comfortable charm.
Less than 60 miles away from Milwaukee — and less than 90 miles away from the Windy City, Chicago — Lake Geneva offers a tranquil escape from big city life and a whole lot of things to do outside. Lake Geneva has four beaches open to the public, ample boating opportunities, a 26-mile long shore path to walk by the lake and numerous historic estates, seven premier golf courses, and the Lake Geneva Ziplines and Adventures complex that’s full of exhilarating surprises. For anyone who wants to take a break inside, Lake Geneva also offers plenty of museums, galleries, theaters, spas, and more.
If you desire a grand stay by the lake, you may want to check out the Grand Geneva Resort and Spa. With five restaurants, two golf courses, a full-service spa, and 356 well-appointed rooms and suites plus a collection of luxury villas, you can easily make a long weekend out of exploring and enjoying this lovely resort.
St. George may only be about 130 miles northeast of the bright lights of Las Vegas and about 300 miles southwest of Salt Lake City, yet St. George very much feels a world away from both. Nature lovers can feast on St. George’s easy access to a wide array of national parks and monuments – including Zion National Park, Bryce Canyon National Park, Red Cliffs National Conservation Area, Gold Butte National Monument, Grand Canyon-Parashant National Monument, and the North Rim of Grand Canyon National Park. For anyone who wants to learn more about the region’s history, you can check out the St. George Dinosaur Discovery Site at Johnson Farm and the St. George LDS Temple which was built under the watch of early Mormon leader Brigham Young.
Situated at the foot of Snow Canyon State Park, and nestled inside the upscale Entrada Country Club, The Inn at Entrada offers 57 studios and suites that offer the comfort of a luxurious Las Vegas resort, the seclusion of a small rural inn, and a convenient location that keeps you close to many of the area’s best attractions. For a good meal any time of day, it’s hard to go wrong at Wood Ash Rye, a chef-driven restaurant with global influences that tells the history of Southern Utah in a very creative and edible way.
About 30 miles north of vibrant downtown Seattle, Whidbey Island offers gorgeous scenery and an interesting local arts and culture scene that makes it easy to forget how close you are to the Pacific Northwest’s largest metropolis. At Deception Pass State Park, you can enjoy 38 miles of hiking trails, three miles of bike trails, over 14 miles of saltwater shoreline, three lakes, three overnight campsites (that are available by reservation), and seemingly endless opportunities to get lost and find yourself in Mother Nature. If you prefer a different kind of exploration, Whidbey Island and nearby Camano Island have plenty of galleries, studios, and museums where you can discover captivating works by local artists.
If you’d like to reconnect with Mother Nature while enjoying some shelter from the harsher natural elements, Cama Beach State Historical Park on Camano Island offers 24 rustic cabins by the beach, two larger bungalows, 15 miles of hiking trails, boat rentals through the Center for Wooden Boats, a park store that’s fully stocked with groceries and supplies, the full-service Cama Beach Cafe, and even WiFi internet in select areas.
Nestled right in between San Francisco and Los Angeles on California’s Central Coast, San Luis Obispo (SLO) County offers a scenic escape from big city life and a unique rustic sophistication that you have to experience yourself to believe. If you’re a dedicated wine enthusiast, SLO County Wine Country features some of California’s most captivating viticultural regions, including Edna Valley near the coast and Paso Robles on the north end of SLO County. If you want to explore beyond the vineyards, SLO County offers tremendous wealth in outdoor treasures — from the easygoing Bob Jones Trail that follows San Luis Obispo Creek to Avila Beach, to the quiet grandeur of Montaña de Oro State Park near Morro Bay, as well as the spectacular land and seascape of Ragged Point and the south end of beautiful Big Sur.
If you’re having a hard time picking where you’re most excited about visiting, it might be a good idea to stay in the center of the action in San Luis Obispo. If you want historic charm, it’s hard to beat the Garden Street Inn in an 1889 Victorian house on land that used to be the Mission Vineyard. If you prefer a more contemporary hotel, Hotel San Luis Obispo offers plenty of postmodern California decor, aesthetically comfy rooms and suites, and Chef Ryan Fancher’s creative twist on farm-to-table cuisine at Piadina and Ox + Anchor.
When it comes to planning Labor Day weekend travel, there are so many possibilities besides the 10 we mentioned above. If we tried to include all of the possible awesome Labor Day trsvel destinations on our list, it might take up the entire internet. So, with that in mind, here are a few more possibilities to check out if you get the itch to travel on Labor Day weekend.
With a thriving arts and entertainment scene, not to mention world-class restaurants, Toronto has something for everyone. Sure, you have to cross the border, but it’s an easy drive from the States. While you’re there. check out the views from the top of the CN Tower and for sports fans, the Hockey Hall of Fame is a must-see.
Since we’re already across the border, we would be remiss not to mention sophisticated Montreal as another great Labor Day weekend travel destination. The old city, with its pubs and French restaurants, gives off a Parisian vibe, and make sure to check out the spectacular city views from Mount Royal Park.
Oregon’s wine country
Sure, California gets most of the attention when it comes to wine, but there are some great wineries up the coast in Oregon. The Willamette Valley has hundreds of wineries to choose from, and those wineries are producing some quality wines. In 2016, Wine Enthusiast magazine named Oregon’s wine country as one of its Wine Regions of the Year.
Generally, when you think of Vail, Colorado, you think of skiing. And that’s fair, Vail is a world-class ski destination. But when the weather is warm, there’s still plenty to do. You can hit the (grassy) slopes for tubing and Alpine coaster rides as well as zip lines. For those who want a calmer adventure, take a gondola ride to the top of the mountain to admire the scenery.
Labor Day Weekend might mark the end of the summer travel season, but that doesn’t mean we have to be sad about it. Think of it this way: We have one more chance to enjoy summer’s finest offerings in early September, then we can plan for our next round of adventures this fall and winter. We might be inclined to shed a few tears when it’s time to pack away our swimsuits, Hawaiian shirts, and Bermuda shorts, but we have one more opportunity to rock our summer fashion this Labor Day Weekend… Then we can plan where we’ll be sporting our favorite winter attire in the months ahead.
We hope you’ve found this guide helpful, and we hope you’re now feeling more inspired to draw your own exciting Labor Day Weekend travel plans. If you want some more help in figuring out which places to add to your future travel plans, check out these great ideas for road trips in Mexico, our Big Bend National Park travel guide, and our Medellín (Colombia) Travel Guide. Wherever you head next, we hope you enjoy the journey.
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