Top 7 Labor Day Trip Ideas: From New England to the Canadian Rockies


Summer may be almost over, which is all the more reason to ensure that your Labor Day is anything but laborious. Take advantage of the long weekend with a holiday abroad, or look closer to home for some weekend festivals to close out the summer season. Whether you’re interested in hiking the Canadian Rockies or setting sail in New England, we’ve got you covered with the best trips to book for the first weekend in September. Read on for the seven places to visit this Labor Day and send summer off in style.

1. Martha’s Vineyard, MassachusettsCliffside in Martha's Vinyard

(Image of Martha's Vinyard provided by Adobe Stock)

New England comes alive in the summertime. While Nantucket tends to get more of the hype these days, Martha’s Vineyard remains an idyllic oasis off the Atlantic Coast of Massachusetts. And there’s no better time to visit than Labor Day, when the island hosts its annual Labor Day Weekend Festival hosted by the Vineyard Artisans. The festival is perfect for collectors and perusers, as it features an array of artwork and crafts from the island’s artists. Finally, be sure to head out to sea while you’re there, as well, as the island’s gorgeous beaches and rolling hills are best appreciated from the bow of a sailboat. 

2. BermudaBermuda shoreline

(Image of Bermuda provided by Adobe Stock)

Bermuda, Bahamas, come on pretty Mama. If that line doesn’t remind you of the Beach Boys — and, hence, put you in the mood for some coastal living — then you’re in more of a desperate need for a palm tree-populated vacation than we thought. Located just off the coast of North Carolina, Bermuda is a tropical retreat that’s in full swing during the summer season (it gets chillier in the wintry months). Labor Day is an ideal time to take a long weekend on-island, as Bermuda is host to an array of marches and parades in celebration of the public holiday.

3. New Orleans, LouisianaThe French Quarter in New Orleans

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A long weekend is the perfect time to take it easy in the Big Easy. While New Orleans is famous for being a hotspot all year-round — there’s always a party happening on these Louisiana streets — Labor Day is a particularly special time to visit, as it is when the annual Southern Decadence event takes place in the city. The annual festival will be held on September 1st to 5th, and features parades, drag shows, live music, and more, in celebration of the city’s LGBTQ+ community. The event draws tourists from all over the world — why not join them this year?

4. PanamaPanama beach

(Image of Panama provided by Adobe Stock)

Animal and adventure lovers alike should venture to the tropical environs of Panama this upcoming holiday weekend. There’s so much more to this fascinating Central American country than just the Panama Canal — though that is one of the seven wonders of the modern world, of course. Head to the Pacific to see whales breaching off the shore — the peak Humpback Whale season is between July and October — or head inland to the rainforests of Portobela to observe sloths in the wild. More of a birder? Hummingbird Station in Gamboa Rainforest Reserve is a veritable paradise. But there’s more to Panama than just animals — the people are what truly make this nation so wonderful and unique. With over seven unique indigenous tribes, this tiny country is a trove of history and culture waiting to be discovered.

5. Big Sky, MontanaMountain in Big Sky

(Image of Big Sky provided by Adobe Stock)

Head to Big Sky Country with a trip out west this Labor Day. Big Sky, Montana, is home to spectacular vistas of the Rocky Mountains, and even more spectacular outdoor activities to pursue in their midst. Big Sky isn’t just for skiing — the off-season of mountain biking, horseback riding, fly fishing, and hiking is just as enticing. Be sure to arrive on Thursday, September 1st, to attend Music in the Mountains, a free outdoor concert series in Len Hill Park. 

6. Charleston, South CarolinaStorefronts in Charleston

(Image of Charleston provided by Adobe Stock)

Famous for its epic culinary scene, gorgeous architecture, and endless nightlife opportunities, Charleston is always a popular destination for weekend visitors. And while it may seem like visiting South Carolina in August is somewhat counter-intuitive, we encourage you to embrace the heat — and feel the music. The Low Country Jazz Festival is an annual event featuring musicians in Charleston, and is taking place on September 3rd and 4th this year. So there’s no better time to enjoy some low country living — and some famous jazz musicians — than this coming holiday weekend. And if you get a bit overheated, just opt for a cruise around the harbor (or visit nearby Folly Beach).

7. Lake Louise, Alberta, CanadaMountain lake in Montana

(Image of Big Sky provided by Adobe Stock)

Head north to experience the wondrous beauty of a Rocky Mountain road trip through Alberta, Canada. The turquoise waters of Lake Louise glisten in the summertime, and you will want the extra days of your long weekend to hike, mountain bike, and horseback ride through the mountainous terrain. Fly into Calgary and rent a car to journey up through Banff towards Lake Louise, and be sure to pack layers. Even though it’s August, it’s still Canada (and you’re still at high altitudes). Trust us, the brisk evenings will come as a refreshing tonic after months of summer heat. Canada is nicknamed the Great White North for a reason, after all. 

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