Last Minute Labor Day Weekend Road Trip

10 Amazing Last Minute Labor Day Weekend Road Trip Ideas

Check out my top picks for an epic Labor Day weekend road trip.

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Well, it’s that time of year again. With Labor Day weekend just a week away in the US, this is when everyone starts feeling the need to make what’s left of summer count. But if you’re like me, planning far in advance for a long weekend can be difficult. They sneak up on you! – No worries though, I’ve got you covered with this list of last minute Labor Day weekend road trip ideas, no matter where home base is for you!

I always love a good road trip. There’s something extra special about loading up the car, curating the perfect playlist, and basically just chilling with your travel partners until you arrive at your destination.

Plus, it’s time we embraced slow travel for the long haul, and a Labor Day weekend road trip close to home is the perfect opportunity to do just that. Or maybe you’ll fly to another region, and check out it’s vibe for your last hurrah of summer – that would be cool too.

Alright, let’s get into it already. I’ve divided this up by region, and compiled two options for each – so you’re bound to find somewhere new and exciting to explore no matter where you’re located!

Car Rentals for Your Road Trip

So you’re flying a few states over to check out a part of the country you’ve never seen before? You’re probably gonna need a car.

If you ARE in need of a car for your Labor Day weekend road trip, look no further than Discover Cars. I’ve always found it to be the absolute best interface for comparing prices, sorting for things like automatic transmission, or weeding out companies I’ve never heard of.

Where to go for a Labor Day weekend road trip


1. Portland, ME

Labor Day weekend road trip to Portland, Maine

Perfect for: Foodies who want a last few days at the beach

Where to stay: This boho chic apartment in the heart of Portland’s West End

We planned a last minute Labor Day weekend road trip to Portland a couple years ago and it couldn’t have been a better choice.

A manageable drive from New York and even shorter from Boston, Portland is hip but also down-to-earth. From quaint New England colonial houses to the picturesque Portland Head Light and Crescent Beach State Park, everything there is to see in and around Portland will have you smitten.

Make sure to grab breakfast at Tandem Coffee or The Holy Donut, and dinner at Little Giant or Duckfat. Oh, and if you do end up in Portland, please. Do yourself a favor and get a lobster roll. Or twelve.

2. Lake George, NY

Labor Day weekend road trip to Lake George, New York

Perfect for: History lovers looking for a little wilderness on the side

Where to stay: This dog-friendly lakeside cabin with panoramic views from the wraparound porch

Lake George – and really the whole Adirondack area – have it all. If you’re basing yourself in Lake George, Fort William Henry is in town, and Fort Ticonderoga is just a short drive away. There’s also a Haunted History Trail you can follow on a tour, or at your own pace! Between the region’s hiking and whiling away long afternoons at the beach, you’ll end up filling all your time and probably not even ticking everything off the list.

If you’re still looking for more for your Labor Day weekend road trip, why not take a steamboat ride on the lake or visit The Wild Center, basically a High Line in the trees, just about an hour and a half drive away.

Be sure to check out the Adirondack Winery, known for using local grapes. I recommend booking ahead. Giuseppe’s Pizzeria & Cafe is also a must for some classic New York pizza.


3. Yellowstone, WY

Labor Day weekend road trip to Yellowstone, Wyoming

Perfect for: Nature and wildlife enthusiasts in need of a few nights under the stars

Where to stay: This cozy log cabin with a private pond and walking distance to a rodeo!! (I am not joking lol)

Haven’t you always wanted to see a geyser erupt and then pet a bison in the same day? Well, you can do one of those things on your Labor Day weekend road trip to Yellowstone. You might come across a bison, but don’t pet it. Seriously. It’s better to look from a safe distance, according to the National Park Service.

Probably the biggest draw of Yellowstone are the geysers and hot springs, and there’s no better place to camp than Madison Campground. You can’t get any closer to the Lower, Upper or Midway Geyser Basins. You’ll also want to check out Old Faithful and Mammoth Hot Springs while you’re in the area.

If it’s animal spotting you’re after, Lamar Valley is the place for you. Just make sure to be there for dawn or dusk to have the best chance of seeing plenty of wildlife action.

Depending on your route in and out of the park, you’ll probably want to take a quick pit stop in Cooke City or Silver Gate – tiny outpost towns with major Old West vibes.

4. Boulder, CO

Labor Day weekend road trip to Boulder, Colorado

Perfect for: A seamless blend of outdoors and city life

Where to stay: This centrally located apartment with a stunning, well-lit breakfast nook

We’ve all been there. Your partner dreams of hiking all weekend. You, on the other hand, would much rather chill with a few beers and people-watch the trip away.

If that sounds familiar, then I cannot wait to send you to Boulder for your Labor Day weekend road trip, which has the best of both worlds. You might even be moved to get out on the trail yourself as you gaze as the beautiful Flatiron mountains overlooking the town. Plus, Boulder is a cyclist’s heaven, so if you get tired of the lush scenery (unlikely) you can always cycle your way through the city. While you’re there you’ll want to make sure you grab a reservation at The Kitchen – a Boulder staple that is not to missed.

Unless you hate yourself you’ll want to stop in for brunch at Lucile’s Creole Cafe (beignets are a must!) and check out the traditional Tajik tea at Boulder Dushanbe Teahouse. Boulder also has a plethora of thrift and vintage shops, which are always a must do when I travel.

If you’re still new to the thrifting game, check out my guide to successful thrifting!

I promise no matter what you want out of your weekend, Boulder will have it and more.

West Coast

5. Joshua Tree, CA

Labor Day weekend road trip to Joshua Tree, California

Perfect for: The dreamers looking for a weekend of relaxation

Where to stay: This secluded (but chic!) cottage nestled among the rocks, or (I couldn’t resist) this luxurious masterpiece of design, if you can get a group together

I am absolutely obsessed with Joshua Tree. When I think about it I conjure up images of beautiful scenery mixed with funky Western flare, mid-century modern decor, and a pinch of celebrity mixed in. The perfect combination for a Labor Day weekend road trip.

Obviously if you’re in Joshua Tree you’ll want to get in a decent amount of hiking, exploring and stargazing, but there is so much more to see than nature! Smith’s Ranch is a totally cute drive-in that will transport you instantly back to the 50’s, as will Pappy & Harriet’s barbecue restaurant. To really shine a light on the eclectic side of Joshua Tree, check out the Hicksville Trailer Palace and Artists Retreat or the Crochet Museum. And last but not least, if you’re there for a taste of the celebrity lifestyle, book yourself in for a sound bath at The Integration.

No matter what side of Joshua Tree you explore, you’re guaranteed to have an amazing time.

6. Seattle, WA

Labor Day weekend road trip to Seattle, Washington

Perfect for: City lovers who want a change of scenery

Where to stay: This tastefully decorated loft/guest house with breathtaking views

I know this isn’t some groundbreaking suggestion – Seattle has been cool. But that doesn’t mean I won’t try to sell you on it anyway! Seattle just screams late summer to me, which is why I immediately thought of it for a Labor Day weekend road trip location.

Bar del Corso is an absolutely must visit, and I have it on good authority that if you don’t get the anchovy toast, you will live to regret it. Obviously you can spend an entire afternoon exploring Pike Place Market, and when you tire of that make sure you head over to Molly Moon’s Ice Cream and get a scoop of Scout Mint.

Seattle has such a diverse food scene, so take advantage of it by hitting up 2C Thai or Poquitos – both of these places are experts at what they do. And it wouldn’t be a trip to Seattle without some seriously amazing coffee, so do yourself a favor and go to Victrola Coffee Roasters where you can even attend free tastings, or Seattle Coffee Works, which works directly with farmers! Or if you want a truly Seattle experience head to what claims to be America’s first coffee cart at Monorail Espresso – I hear the mocha is amazing.


7. Flagstaff, AZ

Labor Day weekend road trip to Flagstaff, Arizona and the Grand Canyon

Perfect for: Honestly literally anyone. The Grand Canyon is objectively for everyone!!!

Where to stay: This colorful and kitschy retreat right in the middle of town

When we went to Flagstaff a few years ago we had initially just seen it as a quick stopover so we could see the Grand Canyon – we had no idea we would love it so much in its own right!

From the great selection at Mother Road Brewing Company, to the homey atmosphere at Oregano’s Italian, or modern vibes at Diablo Burger, there’s actually a lot going on! And that doesn’t even begin to consider the wealth of natural beauty you have at your fingertips. You may not even get to see everything in town what with all the sites.

Obviously the Grand Canyon is the headliner here, as well it should be. It’s a sight to be seen, and I highly encourage everyone to see it at least once in their lives. If you want to try something special you can check out the Grand Canyon Railway – I’m personally dying to do this myself. However, there’s so much more within easy driving distance! You can check out Buffalo Park for a super unique wildlife park experience not unlike a safari, and see the unreal view of Grand Falls in the Little Colorado River.

The beauty in this part of the country is truly unmatched, so no matter what you do I’m positive you’ll be satisfied with a Labor Day weekend road trip to Flagstaff.

8. San Antonio, TX

Labor Day weekend road trip to San Antonio, Texas

Perfect for: Mexican flare without heading south of the border

Where to stay: This brightly colored, centrally located bungalow with a pool and huge outdoor space

I know when people talk about Texas they’ll usually talk about Austin, but I have to say, I think San Antonio is actually the place to be. It has Texas charm, Mexican influence and a very cool industrial vibe. I would go back to San Antonio in a heartbeat, honestly, which is why I’m so pumped to recommend a Labor Day weekend road trip to San Antonio to ya’ll today.

The Pearl is one of the cooler spots in San Antonio. It’s an old brewery that has now been transformed into a space with loads of cute shops and eateries. With places like Cured (a whole restaurant dedicated to cured meats) and Hotel Emma (amazing cocktails, even if you’re not a guest), it’s the perfect place to spend an evening. If you end up there in the daytime though, check out all the shops! I got some of my favorite earrings at a little boutique at The Pearl.

For a very different vibe I would highly recommend The Friendly Spot, who were serving up drinks in a COVID friendly environment before it was cool, and Hot Joy for amazing Asian fusion across the street. And last but not least if you want a truly unforgettable experience check out Mi Tierra for a super traditional (American) Mexican food experience. They’re open 24/7 – need I say more? Mi Tierra is also situated in a super kitsch and cute Mexican craft market, we picked up some of our favorite prints here actually!


9. Savannah, GA

Labor Day weekend road trip to Savannah, Georgia

Perfect for: Anyone with an appreciation for good food and charming views

Where to stay: Honestly I couldn’t even choose all the options were too cute, but this carriage house is up there with the cutest

Oh Savannah, why you gotta be so cute? Southern comfort and Victorian architecture without sacrificing on a bustling city? Sign me up.

While you’re in Savannah you absolutely, no excuses, must go to Mrs. Wilkes Dining Room (doors open at 11am, so get in line folks) and The Olde Pink House. If you can even fathom moving afterwards you can find yourself soaking up some history at the Prohibition Museum or strolling through Forsyth Park. Or if you’re daring you could take a City Ghost Tour… I am not, so I’ll pass.

Savannah is the perfect city for those of us who just want to soak in the energy of the place we’re traveling to. You can spend the whole Labor Day weekend road trip just admiring the beautiful homes and scenery and still feel satisfied. Just do me a favor and eat something delicious for me, will ya?

10. Nashville, TN

Labor Day weekend road trip to Nashville, Tennessee

Perfect for: Music lovers and foodies

Where to stay: This uber chic apartment with the perfect combo of modern and country vibes

I don’t think I need to sell you on why Nashville is cool – the reputation comes with the name. Nashville is one of those cities that makes you wonder why the South gets such a bad reputation. I don’t see anything as cool as Nashville in California – do you?

Nashville is rumored to have introduced the world to the Meat & Three, and if you really want to experience it I’d highly recommend Arnold’s Country Kitchen (open for lunch only!). Lyra is also a very cool and, dare I say ~trendy~ middle eastern spot that has some plates I’m just dying to try. For a cool place to eat that has very general store vibes check out Pucketts Grocery, perfect for Instagram if I’m honest.

Oh yeah and they’re famous for Johnny Cash and the Country Music Hall of Fame… Exciting I guess, but let’s be honest I’m in it for the Meat & Three.

Where are you headed for a last mintute Labor Day weekend road trip?

Writing this post has made me seriously bitter that I don’t have a car. I’m dying to go on a Labor Day weekend road trip!! And I would literally kill to spend a weekend in some of these places.

If you’re heading out to any of these amazing locations, make sure to check all the current local regulations and opening hours! And let me know if you check any of these places out – I want to live vicariously through you.

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    1. Absolutely! I’d say most of these are 100% bucket list worthy, I’m even hoping to go to some of them a second time!

  1. Great article for those who are coming from overseas and want some good local experiences too. These look like fantastic ideas for when we make it back to the US. hopefully the world returns to normal soon and we can book our trip. Seattle may be on the list in particular, so i’ve bookmarked this post for later!

    1. Such a good point – I love getting a more local experience when I go abroad, and a bunch of these are perfect for that! I hope you make it to Seattle soon!

  2. Yes, road trips are in. We just went on a road trip to Blue Ridge, Georgia. Our puppy even got to go. We had a blast. I love your two ideas for the southeast. Savannah and Nashville. Let’s go, I am ready.

    1. Blue Ridge sounds amazing!!! Honestly the South East was so hard to narrow down, so many amazing spots to go to.

  3. These are some great places to take a last-minute road trip to. I’ll be staying home this year to catch up on things, but maybe next year I’ll venture out. Thanks for sharing.

    1. Totally! Things are so complicated right now it’s hard to feel motivated to get out there!

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