Where To See The Prettiest Fall Leaves

With fall being here almost a week, the weather has finally started to cool a bit but not to what it should be. After almost a full week of 90 to 100 degree days, Chicago has sent off summer with brutal temperatures that I never want experience again. The next week is promising with 60 to 70 degree days but for those of us who love to embrace sweater weather, the low 60s/high 50s is where it’s at. Even though the Midwest might be coming off an intense heat wave, one things for certain - the trees are ready for fall. Leaves are falling everywhere and while it’s not peak fall transition yet, it’s enough to get us fall lovers excited for what’s to come. In celebration of the cooler season, we’ve put together a list of destinations across the US to see the prettiest fall leaves. There are hundreds more where this came from so if you don’t see your favorite fall destination on our list, tell us in the comments below! Make sure you also check out our ultimate guide to fall for more seasonal inspiration.

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Boston, MA
Having recently spent a week in this historic city at the peak of the fall season, I cannot recommend enough a visit to Boston during this time of year. The leaves are incredible. Coupled with the cobblestone and brick roads and the historic buildings, it becomes an immeasurable experience. For a true fall experience, stroll through the Boston Common or take a minute to explore Acorn Street in Beacon Hill. You’ll find multi-colored trees throughout the entire city but these two particular spots provide an exceptional experience. If you have time, take a day trip across the river to Cambridge where you’ll experience even more fall greatness. For a bit of a longer hike (about an hour’s drive), head to Salem for the ultimate fall road trip that mixes gorgeous foliage with spooktacular festivities.

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Breckenridge, CO
Located near the heart of Colorado in the Rocky Mountains, Breckenridge is a beautiful site for those lucky enough to live in the area and see it annually each fall. The leaves turn vibrant shades of red, yellow, orange and brown making the scenery seem more like a piece of art rather than real life nature. "The mountains should start seeing leaves change this weekend," says Tiffany of The Dwelling Tree. "Breckenridge and Aspen both have gorgeous fall colors." I've only had the chance to see the mountains in winter with multiple feet of snow but if I have a chance to go back during fall, you bet I'll be taking all the photos I can manage!

Photo c/o Tiffany from The Dwelling Tree

Photo c/o Tiffany from The Dwelling Tree

Galena, IL
Galena is located about three hours outside of Chicago, two or two and a half if you get good traffic. It’s a small, historic city located right on the Mississippi River. It’s a picturesque town with rolling hills and beautiful historic buildings which is magical in the fall. Walk down main street for a middle-America, small town experience with plenty of shops and restaurants to meander through. For those who love hiking, there are trails on trails on trails. While Galena might not be particularly close to...well, anywhere...it is 100% worth the drive. If you happen to plan a fall adventure, you will be welcomed with beauty that only fall can offer both in and out of this incredible city.


Lake Geneva, WI
Known as the summer home destination of wealthy Chicagoans, we prefer this southeastern city in the fall. Located on Lake Geneva, it’s one of those rare spots where fall foliage meets reflecting water. Not only will you build your photography collection while visiting, you’ll also be able to celebrate Oktoberfest, drink loads of cider and beer, go apple picking, roast marshmallows over a bonfire and more. It’s the ultimate Midwestern fall experience that every local to the region must enjoy at least once or twice. My good friend Dannie from Stile.Foto.Cibe. recently wrote a post sharing top fall foliage spots in the Midwest! Make sure you go check it out when you’re finished with our post!

Morton Arboretum in DuPage, IL
Another Illinois gem, the Morton Arboretum in Lisle provides a stunning landscape and natural wonder during the season. They also provide a variety of events all season long for locals and visitors to enjoy. "The Morton Arboretum has an annual fall colors festival when the changing leaves are at their peak," says Katie Matusky of Entropy Organized. "Enjoy miles of hiking through different species of trees, live music, and a candy apple bar. It is an absolutely lovely way to get some fresh air and admire changing foliage from around the world."

Photo c/o Katie Matusky

Photo c/o Katie Matusky

Portland, OR
Representing the western part of the country, Portland seems like the perfect city. Friendly, filled with fantastic food and pretty perfect weather. Average temps are mild for the most part making it my kind of town, especially being a craft coffee mecca. The northwest, in general, is a rather spectacular spot to enjoy fall leaves but if we had to pick one spot Portland wins. Enjoy one of many parks and gardens, browse a bookshop while sipping an unreal cup of coffee, grab a bite to eat (preferably on a patio if you can), go for a hike and enjoy the uniqueness the city offers.

Savannah, GA
Maybe not the most obvious choice for a fall foliage post, I couldn’t leave the south out. While they may experience warm weather more than cool weather, they do experience fall even for a short time. Savannah is one of those places. “The Spanish Moss trees begin to turn as the weather cools,” says Chelsee from Southern Beauty Guide. “It’s particularly stunning at sunset when all the colors come together. Just gorgeous.” Savannah is one of those destinations that is at the top of my wish list. The city is absolutely gorgeous with a vibrant history, beautiful architecture and a booming food scene.

Washington, D.C.
Known more for the cherry blossoms in spring, Washington D.C. should also be noted for their fall colors. Being a little farther south, fall comes a bit later for the capitol but it’s perfect for northerners that want to extend the season a few weeks. I’ve never experienced the cherry blossom trees in spring and I’m sure they’re gorgeous but there was something about walking among the Capitol Building’s grounds and the National Mall in the crisp fall air with leaves falling all around. It was special, that’s the best way to explain it.

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