Fun While There’s Summer Sun: Our Top 10 Labor Day Weekend Trips

August 22, 2014
1. Cape May, NJ: Don't be fooled by MTV: The Jersey Shore isn't all about weightlifting and total debauchery. For evidence to the contrary, plan your next trip to Cape May, located on the southernmost tip of the state's Atlantic coast. Victorian houses are met with scenic miles of beach, making it easy to see why it's been a popular vacation destination for centuries. Pack your sunscreen (and skip the GTL routine) – you'll be spending most of this Labor Day outdoors.

Photo courtesy of Aneese/iStock/Thinkstock
2. Toronto, Canada: Why celebrate a quintessentially American holiday up north, eh? Plenty of reasons: For one, now's the last chance before those Arctic winds start blowing south. Toronto also provides the perfect blend of urban buzz and tranquility. Get your dose of culture (and great eats) in town before retreating to the haven of the Toronto Islands, where you can hike, kayak – or just chill.

Photo courtesy of francisLM/iStock/Thinkstock
3. Hudson River Valley, NY:The Hudson River Valley is technically rural, but given that this is the favorite out-of-town retreat of New Yorkers, you can bet you'll still find coffee shops, artisanal distilleries, contemporary art galleries, and on-trend boutiques. Divide your time between urbane creature comforts and a stay in a rustic cabin. Or a B&B, if you're fancy.

Photo courtesy of alisonperryart/iStock/Thinkstock
4. The Pocono Mountains, PA: If you're a West Coaster, you'll scoff at these gently sloping "mountains," but even if the Poconos don't offer vertiginous heights, they do offer an idyllic long weekend away (well within Ziptrip distance from NYC or Philly). Peppered with lakes and cabins aplenty, this getaway is best enjoyed with a group. Speed freaks may also want to make a pilgrimage to Pocono Raceway, where many driving greats have burned rubber.

Photo courtesy of Nicholas A. Tonelli/Flickr
5. Chicago, IL: More of an urbanite than a wannabe mountaineer? Late summer is the perfect time to stop by Chicago, before another polar vortex freezes Lake Michigan solid. It's also prime festival season: The North Coast Music Festival will cater to contemporary music fans, while the classic Chicago Jazz Festival is returning for its 36th year. Catch some experimental theater at the Chicago Fringe Festival before noshing on kielbasa at the Taste of Polonia Festival.

Photo courtesy of the City of Chicago
6. Denver, CO: If even the bunny slopes are too challenging for you, visit Denver before ski season gets underway. There’s plenty to do in the Rocky Mountain city at summer’s end, like ziplining, an adrenaline rush with a view. You can also stop by the Taste of Colorado food festival to sample local specialities, or just take in the scenery from the ground in your Zipcar.

Photo courtesy of Taste of Colorado
7. Harpers Ferry, WV: D.C. still feeling swampy in August? Head out to Harpers Ferry, where you can bone up on some Civil War history. With origins going back to the 18th century, Harpers Ferry has a movie set-like historic downtown, and sits on the edge of a national park of the same name. Go for a trek and then indulge in some southern-style eats – like the John Brown at Canal House Café, a pulled beef sandwich served on cornbread.

Photo courtesy of Steven Heap/iStock/Thinkstock
8. Block Island, RI: Rhode Island isn't an island, but Block Island in Rhode Island is. Got it? Good. Now catch a ferry over for an instant hit of New England's bucolic best. When you're not bodysurfing along the white sand beaches, take on the role of professional lobster roll eater.

Photo courtesy of kschulze/iStock/Thinkstock
9. Cape Cod, MA: For New Englanders, Cape Cod is the byword for summertime retreat. This isn't an under-the-radar getaway, of course – Cape Cod is notorious for its traffic snarls – but make plans to head out early and be rewarded with a weekend of beaches, Adirondack chairs, and art, wine, and food festivals.

Photo courtesy of cindygoff/iStock/Thinkstock
10. Milwaukee, WI: River kayaking, brewery tours, and custard stops: With its Americana staples, Milwaukee may well be the perfect place for a festive Labor Day weekend. Not to mention the fact that the city plays host to the Harley-Davidson Milwaukee Rally every Labor Day. It doesn't get more American than that.

Photo courtesy of Jim Bauer/Flickr
1. Cape May, NJ: Don't be fooled by MTV: The Jersey Shore isn't all about weightlifting and total debauchery. For evidence to the contrary, plan your next trip to Cape May, located on the southernmost tip of the state's Atlantic coast. Victorian houses are met with scenic miles of beach, making it easy to see why it's been a popular vacation destination for centuries. Pack your sunscreen (and skip the GTL routine) – you'll be spending most of this Labor Day outdoors.

Photo courtesy of Aneese/iStock/Thinkstock
2. Toronto, Canada: Why celebrate a quintessentially American holiday up north, eh? Plenty of reasons: For one, now's the last chance before those Arctic winds start blowing south. Toronto also provides the perfect blend of urban buzz and tranquility. Get your dose of culture (and great eats) in town before retreating to the haven of the Toronto Islands, where you can hike, kayak – or just chill.

Photo courtesy of francisLM/iStock/Thinkstock
3. Hudson River Valley, NY:The Hudson River Valley is technically rural, but given that this is the favorite out-of-town retreat of New Yorkers, you can bet you'll still find coffee shops, artisanal distilleries, contemporary art galleries, and on-trend boutiques. Divide your time between urbane creature comforts and a stay in a rustic cabin. Or a B&B, if you're fancy.

Photo courtesy of alisonperryart/iStock/Thinkstock
4. The Pocono Mountains, PA: If you're a West Coaster, you'll scoff at these gently sloping "mountains," but even if the Poconos don't offer vertiginous heights, they do offer an idyllic long weekend away (well within Ziptrip distance from NYC or Philly). Peppered with lakes and cabins aplenty, this getaway is best enjoyed with a group. Speed freaks may also want to make a pilgrimage to Pocono Raceway, where many driving greats have burned rubber.

Photo courtesy of Nicholas A. Tonelli/Flickr
5. Chicago, IL: More of an urbanite than a wannabe mountaineer? Late summer is the perfect time to stop by Chicago, before another polar vortex freezes Lake Michigan solid. It's also prime festival season: The North Coast Music Festival will cater to contemporary music fans, while the classic Chicago Jazz Festival is returning for its 36th year. Catch some experimental theater at the Chicago Fringe Festival before noshing on kielbasa at the Taste of Polonia Festival.

Photo courtesy of the City of Chicago
6. Denver, CO: If even the bunny slopes are too challenging for you, visit Denver before ski season gets underway. There’s plenty to do in the Rocky Mountain city at summer’s end, like ziplining, an adrenaline rush with a view. You can also stop by the Taste of Colorado food festival to sample local specialities, or just take in the scenery from the ground in your Zipcar.

Photo courtesy of Taste of Colorado
7. Harpers Ferry, WV: D.C. still feeling swampy in August? Head out to Harpers Ferry, where you can bone up on some Civil War history. With origins going back to the 18th century, Harpers Ferry has a movie set-like historic downtown, and sits on the edge of a national park of the same name. Go for a trek and then indulge in some southern-style eats – like the John Brown at Canal House Café, a pulled beef sandwich served on cornbread.

Photo courtesy of Steven Heap/iStock/Thinkstock
8. Block Island, RI: Rhode Island isn't an island, but Block Island in Rhode Island is. Got it? Good. Now catch a ferry over for an instant hit of New England's bucolic best. When you're not bodysurfing along the white sand beaches, take on the role of professional lobster roll eater.

Photo courtesy of kschulze/iStock/Thinkstock
9. Cape Cod, MA: For New Englanders, Cape Cod is the byword for summertime retreat. This isn't an under-the-radar getaway, of course – Cape Cod is notorious for its traffic snarls – but make plans to head out early and be rewarded with a weekend of beaches, Adirondack chairs, and art, wine, and food festivals.

Photo courtesy of cindygoff/iStock/Thinkstock
10. Milwaukee, WI: River kayaking, brewery tours, and custard stops: With its Americana staples, Milwaukee may well be the perfect place for a festive Labor Day weekend. Not to mention the fact that the city plays host to the Harley-Davidson Milwaukee Rally every Labor Day. It doesn't get more American than that.

Photo courtesy of Jim Bauer/Flickr