Looking for the best Labor Day weekend trips? This is the guide for you!
Long weekends are one of the best ways for teachers and other full-time professionals to take advantage of travel.
Labor Day weekend is especially an amazing time to travel thanks to prime weather around the United States and a quick pick-me-up after official summer vacation has ended.
This round-up post features top Labor Day weekend destinations from travel bloggers across the United States, sharing details of why each of these vacations is great.
Consider unique destinations like the Olympic Peninsula or Martha’s Vineyard for less crowds than the traditional summer season.
Quirky cities like Portland draw budget travelers for a fraction of the cost that summer months see. Or get off the beaten path in towns you’ve never heard of, like Put-in-Bay or Catawba!
No matter where you choose, this guide details everything you need to know- from how to get there, when to book your trip, and lots of hotel recommendations.
Let’s dive into the best Labor Day weekend trips in the USA!
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American West
1. Olympic Peninsula
Best for: Budget
Make your way to Washington State’s Olympic Peninsula for a budget-friendly weekend break.
While you won’t see summer crowds, you should still expect to see Puget Sound Locals making their way to the peninsula for the Labor Day weekend break.
Lush, green forests, the idyllic Hood Canal scenery, fresh oysters, and quiet hiking trails – what more could you want?
Sure, it’s not exactly sunbathing weather yet, but you can still head to Lake Cushman and dip your toes in the lake or just sit out and enjoy the epic scenery.
A Labor Day weekend trip can be booked last-minute, but try to reserve your accommodation as soon as possible because there’s not a ton of inventory.
Campgrounds are top-notch, and you’ll find a selection of vacation rentals available. If you’re looking for a waterfront stay, book The Waterfront at Potlatch.
Some of the best things to do over Labor Day Weekend are:
- Hiking in the Olympic National Forest. We love the Staircase Rapids Loop hike.
- Hike at Olympic National Park
- Kayaking or relaxing beach-side at Lake Cushman.
- Wandering the small center of Hoodsport
You’ll need a car to explore the area, and if you’re flying into Sea-Tac airport, it’s easiest to rent one there.
You can then make your way to Hoodsport/Lake Cushman/Staircase via the I-5, or for a little more adventure, drive up to Seattle, take the ferry to Bremerton, and drive along the southern part of the Hood Canal (it takes about an hour longer, but the scenery’s worth it!).
Tip: don’t miss Olympic Mountain ice cream at Hoodsport Coffee Company!
Stay: The Waterfront at Potlatch
Contributed by Candice of Go See Learn
2. Portland
Best for: Pacific Northwest sunshine
Portland, Oregon is a great destination for a weekend getaway, but especially over Labor Day.
You’ll miss the summer crowds and prices, while still enjoying decent weather. September has a lower chance of rain compared to the following months. So it’s a perfect combination.
As a traveling foodie, my favorite thing to do in Portland is a walking food crawl of the best downtown Portland spots like Stumptown Coffee, Multnomah Whiskey Library, Bamboo Sushi, and Deschutes Brewing.
Be sure to also take some time to walk around the waterfront and soak up the Pacific Northwest nature. The Moxy Hotel Downtown is a great option for close proximity to these local spots at a decent price.
You can experience Portland without a car by easily taking the MAX (local above-ground metro) to and from the airport and around town.
But if you rent a car, consider spending an afternoon driving east to Multnomah Falls and The Columbia Gorge. The views are stunning!
Or if you’re up for a hike, tackle the 2.6-mile round-trip switchbacks that take you straight up to the top of the 620-foot falls.
Trust me, it will be a highlight of your Labor Day weekend vacation and a sight to remember!
Stay: The Moxy Hotel Downtown
Contributed by Hannah of Plate & Compass
3. Denver
Best for: Weather
So many things make Denver special. From its craft breweries to its outdoorsy locals to the famous Red Rocks Amphitheatre, it’s easy to see why people visit Denver and immediately fall in love.
My favorite days in Denver are usually spent just strolling in the River North Arts District, grabbing coffee or drinks or even getting a little work done on my laptop.
Although Denver is not in the mountains, the Rockies are never far. You can enjoy incredible mountain views from downtown, and you can access amazing hikes from Boulder. Boulder is only a 45-minute drive from Denver – perfect for a partial day trip.
September is my absolute favorite time of year in Colorado. The weather is just starting to cool off, so the days are warm, with pleasantly cool evenings.
It’s all of the best parts of the summer, but never too hot to comfortably be outside.
Watch for flash sales from airlines for the best deals; Denver experiences year-round tourism and expensive airfare prices in both summer and winter.
Be prepared to rent a car to explore the city, visit Red Rocks Amphitheater, and get into the mountains for some hiking.
Most any trip to Denver will run on the expensive side, but Labor Day falls during the shoulder season so prices should dip slightly.
One Denver hotel well worth considering for a budget-friendly trip is the Slate Hotel Denver Downtown, which has a great location just off of the 16th Street Mall near popular bars and restaurants.
Tip: Be sure to also try some of Denver’s iconic restaurants like City O’ City and Linger.
Stay: Slate Hotel Denver Downtown
Contributed by Amber of Amber Everywhere
East Coast Labor Day
4. Martha’s Vineyard
Best for: Relaxation
Labor Day weekend is the sweet spot for visiting Martha’s Vineyard. August crowds have dwindled and the atmosphere is more relaxed. Daytime weather is warm and sunny, with cooler evenings.
Get to the island via ferry from Woods Hole. When you arrive, local bus transport is reliable and inexpensive.
One thing I love about Martha’s Vineyard is that a 3-day weekend is a good amount of time to see most of the island.
The most efficient way to see all of the key sites is by taking a 4-6 hour island tour! It takes you through the full island.
A highlight of the weekend is the Vineyard Artisans show. It’s the largest art show on the island and features clothing, ceramics and jewelry from local artists.
I also recommend a visit to the fishing village of Menemsha to enjoy a fresh lobster roll and catch the stunning sunset at the beach.
Hotels and restaurants can be expensive on Martha’s Vineyard, however there is a highly-rated hostel on the island. Aim to book 2-3 months in advance.
Many of the main attractions on the Vineyard are free of charge or under $10, such as the Aquinnah Cliffs, Flying Horses Carousel and Edgartown Lighthouse Beach.
The main towns of Oak Bluffs and Edgartown are fully walkable with shops, restaurants and beaches all close to each other so no need for renting a car!
Tip: Super short on time? You can also make it a day trip from Boston
Stay: Martha’s Vineyard Hostel
Contributed by Maria of Martha’s Vineyard Travel Tips
Midwest
5. Chicago
Best for: Iconic
In early September, Chicago typically experiences pleasant weather, with warm temperatures during the day and cooler evenings.
It’s an ideal time to explore the city without the sweltering heat of summer or the chill of winter.
With the mild weather, you can enjoy various outdoor activities. Take a leisurely stroll along the Lakefront Trail, rent a kayak or paddleboard on Lake Michigan, or have a picnic in one of Chicago’s beautiful parks like Millennium Park or Grant Park.
Labor Day weekend in Chicago is often packed with events and festivals. From music festivals like North Coast Music Festival to the Chicago Jazz Festival, there’s something for every taste.
Additionally, you might catch the Chicago Dancing Festival or the Taste of Polonia Festival, showcasing the city’s diverse cultural scene.
Looking for spectacular views? Head to a local rooftop or splurge on some Skydeck tickets (I think it’s well worth the cost on a clear day)!
While Chicago is undoubtedly popular during Labor Day weekend, it might not be as crowded as other major holidays like Independence Day.
However, it’s still advisable to book accommodations and tickets for events in advance to avoid any last-minute hassles.
Prices for accommodations and activities might be slightly higher due to the holiday weekend, but with proper planning, you can still find good deals.
Overall, Chicago offers a perfect blend of culture, entertainment, and outdoor activities, making it a great choice for Labor Day weekend getaway.
Tip: If you love the outdoors, you can also plan for hiking near Chicago at places like Starved Rock State Park or Indiana Dunes National Park.
Stay: Felix Hotel
6. Shores and Islands, Ohio
Best for: Seasonal
The Shores and Islands region of Ohio sits along Lake Erie and is conveniently only an hour from Cleveland and an hour and a half from Detroit.
It’s especially lovely for Labor Day because this area is a seasonal one, meaning many of the activities, shops, and restaurants either close down or have reduced availability after summer.
Labor Day marks the end of their season, so not only can you enjoy everything right before everything slows down, but the weather is still nice and there are lots of fun events to celebrate the close out of the season.
Not only that but it is a relatively compact area so you can do a lot with just a weekend itinerary for Shores and Islands, Ohio.
Shores and Islands is also special because it can be exactly what you want to make of it.
Want a relaxed feel? There’s lots of beaches, wineries in Catawba, and cute, boutique stays, especially in Lakeside Chautauqua.
Looking for a party vibe? Take a ferry to Put-in-Bay, stay in a budget hotel, and sample their many bars like Last Resort Engine Company on an actual fire engine!
A rental car is certainly necessary as it’s easiest to get around the area by car. On the smaller islands, like Put-in-Bay, you can rent a golf cart to get around for the day.
For Labor Day, you should book a couple months in advance because it’s the end of the season and the extended weekend naturally draws out even more travelers.
Don’t miss the Marblehead Lighthouse, Twin Oast Brewing, and Perry’s Victory and International Peace Memorial.
Stay: Lakeside Chautauqua
Contributed by Alanna of Periodic Adventures
7. Milwaukee
Best for: Compact
Milwaukee is an excellent choice for a Labor Day getaway, and it’s easy to see most of the city’s sights during a long weekend. Plus, the weather is perfect this time of year, and the days are still long, so you have plenty of time to explore.
Fly into the Milwaukee Mitchell International Airport, located just a few miles south of the city center.
I love that Milwaukee is a very walkable city, so you won’t even need a car to see most of Milwaukee’s top attractions. (Unless you plan to visit the Mitchell Park Domes, or to catch a Brewers baseball game at American Family Field!)
I’m a big fan of visiting museums. If you love fine arts, don’t miss the Milwaukee Art Museum – just the building architecture is stunning!
Or check out the world’s only Harley-Davidson Museum. A unique way to experience the city is on a pedal tavern tour!
Hungry? Enjoy hearty favorites like brats and fried cheese curds (and a local brew) at Mader’s, then take an after-dinner stroll along the downtown RiverWalk and look for the Bronz Fonz.
Milwaukee hotels are reasonably priced, so a trip here won’t blow the budget (book a couple of months in advance to get the best deals).
Milwaukee additionally makes for a pleasant spring break or Midwest road trip.
Stay: Plaza Hotel
Contributed by Lisa Garrett from Waves and Cobblestones
Beach
8. San Diego
San Diego is a city near the US-Mexico border that has a lot going for it. First of all, it boasts some of the best weather in the United States.
With its mild, Mediterranean climate, it’s almost always sunny and pleasant, with warm summers and mild winters.
Labor Day is a perfect time for your trip to San Diego. There are many events that take place only during this time of the year.
You can attend Sand Sculpting Challenge & Dimensional Art Exposition that takes place at Broadway Pier & Landing to see three-dimensional art from sand.
Another highlight of Labor Day in San Diego is the concert by the San Diego Symphony that takes place at Embarcadero Marina Park South.
In other words, Labor Day is a perfect time to experience the real spirit of San Diego with local events, concerts and social gatherings.
If you are a beach lover like me, you will love San Diego. The city has over 70 miles of coastline, where you can sunbathe, surf and enjoy the perfect weather.
You can fly into San Diego International Airport (SAN) or drive to San Diego, or if you are in California or in the Southwest.
While San Diego has some public transportation options, it’s best to rent a car for your trip, especially if you want to visit places like Potato Chip Rock or Torrey Pines State Natural Reserve Park.
Since San Diego is a relatively expensive destination, book your accommodations at least a few weeks ahead of your trip.
Stay: Sofia Hotel
Read Next: Santa Barbara, Joshua Tree, Alabama Hills
Contributed by Daria of Explore Baja California
Conclusion
From the serene shores of South Padre Island to the historic charm of Put-in-Bay, the United States features tons of getaway destinations perfect for Labor Day Weekend.
Whether you’re seeking a beach retreat, a cultural city break, or a taste of midwestern hospitality, there’s something for everyone.
For the best compact walkable city, consider Milwaukee for a rich blend of art, history, and culinary delights.
The quiet allure of Lakeside Chautauqua offers a peaceful respite for those wishing to escape the hustle and bustle.
These destinations not only promise memorable experiences but also the opportunity to create lasting memories over the long holiday weekend.
