Last updated on December 5, 2024. Original publish date: September 6, 2017

Top Cities You Didn’t Know You Had to Visit This Fall

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Fall, the season of long pants and a cool, crisp breeze, and campfires under the stars. A time of year you never want to end. But your fall doesn’t have to be relegated to the well-grooved tourist tracks of New York, Los Angeles, Grand Canyon, and the like. Instead, take the road less traveled and make the fall unforgettable when you discover these underrated hidden gems.

Portland

Portland is where young people go to retire, so you’ll find no shortage of places for chillaxing on this fall. With endless urban and outdoor adventures, Portland is an up-and-coming destination perfect for every traveler.

Beer and bicycling is the Portland way of life. For the ultimate Portland experience in the heart of the city, head to BrewCycle for a pedal powered ride with lots of local beer served along the way. Starting at their nano–brewery Back Pedal and pedaling to the trendy Pearl District, the BrewBarge cruises along Willamette, a perfect time for photo ops of lovely city views. Riders can bring their own beer on board as they power the barge by peddling.

Another Portland staple is the Hollywood Theatre, a historic landmark that was built in 1926. This popular non-profit seeks to entertain and promote the art of film, which is always better with beer (yes, we really like our beer) and pizza. If you can’t fit a full movie into your schedule, check out their new airport movie theater at the Portland airport that shows short films produced around Oregon.

The locals like to joke that it rains twice a year in Portland: October through April and May through June. In other words, it rains a lot, but don’t let that stop you from the excitement and thrill of skydiving. At ifly Indoor Skydiving, anyone ages 3 to 103 can partake in experiencing a rush of adrenaline in a completely safe and controlled environment. iFly is great for the whole family and an unforgettable experience.

If you’re lucky enough to get a sun break from the clouds, get back to nature in the cute town of Silverton, home of the Oregon Garden. Conveniently located just an hour south of Portland, this stunning 80-acre botanical garden showcases the area’s natural wonders. Garden lovers can revel in the beautiful greenery of 20 specialty gardens, including the Children’s Garden, Northwest Garden and Conifer Garden.

If you’re in the mood for some dining alfresco on the patio, check out Line & Lure Kitchen, the perfect place for enjoying stunning views while sampling the best of local seafood-to-table specialty dishes like lobster and shrimp boils. Close by is the Michael Jordan Steakhouse, which serves up steak that matches the quality of MJ’s iconic brand and career.

Napa Valley

An excellent spot for a picnic in the countryside is Napa Valley, especially in the late summer, which promises beautiful weather, vineyards heavy with grapes, and scenic views. No trip to Napa is complete without a sampling of the region’s famous wines, but the experience at CADE Estate Winery takes wine tasting to a whole other level. Located on Howell Mountain, it’s known as one of the best wineries in the area, boasting incredible views of the valley and a modern, chic design that promotes sustainability. Enjoy your tasting experience in their stylish tasting lounge, outdoor courtyard patio, winery terrace, or custom-built cave.

Colorado Springs

With views of Pikes Peak from anywhere in the city, Colorado Springs is the home of America’s Mountain, which helped inspire its number one rating for nature parks on Trip Advisor. The area offers easy access to outdoor activities, including the popular Royal Gorge Bridge & Park, which features the best whitewater rafting in the country. If you’d rather stay dry, the park also features thrill rides, waterfall hikes, rodeos, professional cycling races and more. Another must-see is the Garden of the Gods visitor and nature center. Start your adventure with a front range rock climbing session or play it safe on a jeep tour or hiking expedition. With endless blue skies, it’s always a great day to be outside in Colorado Springs. Learn more at visitCOS.com.

Manassas, Virginia

Escape the chaotic pace of urban life and enjoy a more relaxed and low-key vibe when you make a pit stop in charming small towns surrounded by beautiful outdoor scenery. Just 30 miles from Washington DC, Prince William and Manassas is the perfect getaway and only an hour and a half drive away.

Nearby is the historic Occoquan, an old mill town nestled along the tree-lined Occoquan River. Besides its peaceful natural setting, you’ll also find dozens of unique locally owned restaurants and shops. A favorite activity is live music at the River Mill Park, which also hosts family-friendly events like the annual Lemonade Stroll in July.

San Luis Obispo, CA

The cultural and entertainment hub of California’s scenic Central Coast, San Luis is a vibrant college town with a youthful and creative vibe that regularly attracts superstars like Willie Nelson and Snoop as well as top classical music acts in the country. The town’s low profile makes it a welcome respite for travelers (and famous types) who want to experience an easy-going lifestyle in a pleasant Mediterranean climate. Make sure to check out the thriving nightlife and cultural scene in the award-winning downtown area, a great place to get acquainted with this charming town. Another popular activity among locals and visitors alike is the Concerts in the Plaza series, which offers free live music ranging from Indie Pop and Reggae to Celtic Rock and Afro-Caribbean jams. Learn more at sanluisobispovacations.com,

This season, enjoy the cool days of the fall in these tucked-away destinations that are far removed from the hectic pace of major tourist hotspots.

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