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4 trips to take this fall

Updated: Sep 21, 2019

Fall is the perfect time to take the trips you couldn't fit into the busy and expensive summer travel season. Whether you’re ready for pumpkin spice or looking to extend your endless summer, the following are for trips you need to take this fall.


Chicago, IL

Chicago gets a lot of press for its bipolar weather but despite sweltering summers and arctic winters, it’s a beautiful place to spend time outdoors just before the weather dips below freezing. This makes autumn one of the best times to visit the Windy City.


While it will most likely be too cold for a swim, a bike ride along Lake Michigan’s coast is an absolute must. After taking in the city’s skyline, explore some of its architectural landmarks up close like the Bean and Millennium Park then grab a ticket to one of the city's architectural boat cruises.

Chicago’s food scene is one of the county’s best so check out some of the its most highly rated restaurants which can be found in the Logan Square and Fulton Market neighborhoods.


While you’re there, it’s worth trying to secure entry to the posh new Soho House. While the rooftop pool will likely be closed. You’ll still be able to enjoy dinner overlooking city’s beautiful skyline.


Boston, MA

New England is notorious for its autumns and Boston is one of the best places to see the seasonal change. Its historic neighborhoods are lined with cobblestone sidewalks and breathtaking brownstones that pair perfectly with the shades of auburn that come with the fall.


Boston makes for a perfect trip over a long weekend and has quite a bit of activity despite its small town feel. Check out its buzzing food scene in South End, Back Bay or Somerville or visit one of its countless museums and historic landmarks. The city is very walkable but starting the weekend with a Duck Boat tour will help you get the lay of the land and figure out which sites you can't miss. And for the sports fans if you plan it well enough, you can align your trip to catch a Patriots game at Gillette Stadium.


While in the city, be sure to walk through the public garden and Boston Common but if you really want a vast landscape of changing leaves, drive just 25 minutes south of the city for at hike at Blue Hills Reservation. You won't be disappointed once you reach the top.


Paris, France

After spring, autumn is one of the best times to visit Paris. The majority of tourists are long gone with the heat, freeing up the city for those looking to experience a more laid-back side of Paris.


Once you’ve ticked off all the tourist attractions, Paris is a great place to enjoy life the way you would back home while connecting with the city’s culture. Enjoy picnics in the Luxembourg garden or a stroll through the charming Marais neighborhood while popping in and out of vintage boutiques and sampling one boulangerie after the next. Drop by the Pompidou Modern Art Museum or one of the many other chic galleries in Saint Germain Des Pres. From there it’s on to an intimate dinner in the Premier Arrondissement or somewhere in Bastille.


For the lifestyle traveler, few places can beat Paris on any day, let alone when Parisians are at their chicest and most camera ready. So grab your scarves and wool coats; the city of lights is the perfect backdrop for your fall getaway. Check out our guide to see the best neighborhoods to stay while visiting Paris.


Upstate New York

It’s easy to forget that just a few hours drive north of New York City skyscrapers are replaced with towering trees and mountains ranges like the Adirondacks. If you’re looking to escape the Big City madness while taking in the fall foliage, take a trip upstate and discover another, beautiful side of New York.


There are plenty of options when it comes to selecting a town and a broad range of activities in each of them. For a really immersive retreat upstate, Hunter Mountain in the Catskills region is beautiful and has plenty of hiking trails, zip lining and waterfalls for the nature lovers. Further up north you have Lake Placid, a stunning town in the Adirondack Mountains and a few more hours to the west and you'll find yourself in Ithaca, a popular town known for its vibrant young culture and beautiful Lake Cayuga.


If it’s a cultural Upstate experience you prefer then the wineries in the Finger Lakes region are a must. And for the art lovers, Storm King is a breathtaking 500-acre outdoor museum featuring sculptures from artists around the world. Visitors can choose to bike from one sculpture to the next or simply wander aimlessly taking in the vibrant hues of the surrounding trees.