7 Fun Destinations for Cooler Weather

Pumpkin spice is in the air, and outdoor adventures are calling! There’s no better time than now to put on your coziest sweater and head out of town for a dose of fall fun. And from vibrant foliage to seasonal treats, our favorite destinations for cooler weather offer the very best of the season.

Ready to create epic autumn memories? Head to one of these cities for a fantastic fall getaway!

• Alexandria, VA

  This historic city absolutely shines in the fall!

  Tucked along the Potomac River, Alexandria is filled with outdoor sights and activities. And the cool-not-cold autumn months are the perfect time for enjoying them! Throw on your favorite hoodie and visit farmers’ markets, cafes, and galleries.

  Old Town Alexandria is especially charming, with its cobblestone streets and historic architecture. Then stroll along the waterfront for a delicious seafood meal, with stunning views of the changing leaves.

• Boulder, CO

  Does the first sign of cooler weather have you running outside for fresh air? Then add Boulder to your list of cool weather destinations!

  Boulder is a paradise for nature lovers and outdoor enthusiasts. Fall temps are perfect for enjoying the scenic hiking trails. And the golden aspens create stunning views at popular spots such as Chautauqua Park and the nearby Flatirons.

  The city is also known for its thriving craft beer scene. After a day of outdoor adventures, you can cozy up with a locally brewed seasonal ale (or two!).

• Burlington, VT

  New England is full of amazing destinations for cooler weather; Burlington stands proudly at the top of that list!

  Its location, on the shores of Lake Champlain, offers breathtaking views of the surrounding mountains and their vibrant fall colors. Take your pick between hiking, apple-picking, or good ol’ leaf-peeping.

  Explore unique local shops and cafes at Church Street Marketplace, recently voted “The Best Public Square in America.” Don’t forget to enjoy Vermont’s famous farm-to-table cuisine!

  Pro Tip: Bundle up! With its lakefront location and northern air, Burlington gets downright chilly.

• Hood River, OR

  Coffee, anyone? Hood River is known for its foodie offerings, especially locally roasted coffee offered in the city’s cafes.

  But that’s not what makes it one of our favorite destinations for cooler weather. It’s the orchards! Specifically, apples and pears, which are ripe, delicious, and just perfect for that classic fall outing.

  Hood River is tucked into the Columbia River Gorge, where windsurfing and kiteboarding are popular all year—yes, even in the cool autumn weather! If you guys would rather stay warm, check out the hiking trails through the gorge. The spectacular waterfalls, framed by fall foliage, will take your breath away.

• Madison, WI

  Looking for a fall destination that’s under the radar?

  Surrounded by lakes, parks, and fall foliage, Madison is an underrated gem. Try hiking, biking, or visiting the University of Wisconsin’s Arboretum for close-up views.

  Despite being less talked about than some of the other fall hotspots, Madison offers a wealth of activities. Harvest festivals, live music, and the Dane County Farmers’ Market all come together for an unforgettable autumn experience.

• Providence, RI

  Get ready for an epic blend of coastal beauty, a rich food scene, and stunning foliage!

  Forget everything you may think of when you envision big cities in the Northeast. Providence is brimming with green space, ummm, make that red-orange-gold space! And the Providence River runs right through downtown, adding to the fresh, open feel of the city.

  Providence is also known as a food lover’s paradise, with culinary hotspots focusing on seafood, farm-fresh eats, and ethnic cuisine.

• Savannah, GA

  We’ll end our list with an unexpected twist: one of our favorite Southern destinations for cooler weather.

  The mild days and cool nights are perfect for enjoying Savannah’s charm and culture. And the city’s walkable, waterfront layout is perfect for exploring the cobblestone streets and diving into the delicious Lowcountry cuisine.

  If you’re a history buff, a guided walking tour is a fun way to peek into the city’s path and visit the city’s historic mansions and squares. Local guides have plenty of stories to tell!

  Pro Tip: With its warmer weather, the best fall foliage in Savannah takes place later in the year than the other spots on our list—perfect for a late autumn getaway!

Whether you’re into outdoor adventures or simply enjoying the season, these destinations for cooler weather are the perfect backdrop for fall fun!

And to keep the emphasis on fun, ship your stuff to your hotel or Airbnb with LugLess. No hauling bags at the airport, no wasted autumn minutes at baggage claim. So you can arrive at your fall destination rested, relaxed, and ready to do some serious leaf-peeping!