September Is a Great Time to Go Road Tripping

Ask any experienced traveler, and they’ll tell you that September may be one of the best months of the year to explore new destinations. As fall rolls in, summer travelers have headed back home, making highways, airports, and popular locales much less crowded. In many places, the August heat has given way to cooler, more pleasant temperatures. Travelers can also find great deals on flights, tours, and accommodations once summer has ended. Best of all, some locales seem to shine their brightest in September.


01 The Berkshires, Massachusetts

Some say they travel here for the crisp mountain air. Others claim it’s the magnificent vistas of the Berkshires and Western Massachusetts. For decades, people have chosen this destination to escape the hustle and bustle of city life. In September, the area is still lush and green, and its magnificently colored fall foliage is just starting to emerge. Antique stores, coffee shops, galleries, and boutiques are plentiful in the quaint little towns that dot the Berkshires. Enjoy all the outdoor activities in September’s mild 65-75 degree temperatures, whether it’s hiking, biking, kayaking, or exploring.

02 Woodstock, Vermont

Vermont is one extended scenic drive, with picture-perfect views no matter where you look. Woodstock, in central Vermont, is breathtaking year-round, but the fall is especially gorgeous. Cobblestone sidewalks, unique clothing and culinary stores, art galleries, craft breweries, and artisan shops fill its quaint town center. Lovers of the outdoors will marvel at the sight of the Quechee Gorge, the dense forests, peaceful rivers, quiet country roads, and covered bridges. September temperatures are in the mid and upper 70s and fall into the upper 60s towards the end of the month.

03 Grand Canyon, Arizona

Few landscapes on the planet are as spectacular, colorful, and awe-inspiring as those in the Grand Canyon. Weather varies in the canyon due to its drastic elevation changes, but temperatures are coolest on the canyon floor. The Colorado River, which cuts through the canyon, is warmer in early September, making it perfect for those who enjoy water adventures.

04 Telluride, Colorado

Telluride has some of the most scenic vistas in the country. A box canyon surrounds the town, with spectacular 13,000-foot mountain peaks on all sides. Colorful Victorian homes, clapboard storefronts, and historic architecture make up the town’s center. In mid-September, the leaves on the aspen trees transform into shades of golden yellow. Over the next few weeks, the area explodes with vibrant autumn colors. High daytime temperatures are usually in the upper 60s.

05 Augusta, Georgia

Although it can be rainy, warm, and humid in September, Augusta’s fall weather is comfortable. Plus, the less-than-ideal weather means savings on accommodations and other travel-related costs. This city is the second oldest in the state, so history-related activities and landmarks are available throughout the city. Broad Street, a revitalized downtown community, is home to innovative eating establishments and interesting stores. You’ll also find hand-crafted glass and pottery at one of the many artisan shops.

06 Eureka Springs, Arkansas

This little gem in the heart of the Ozark Mountains is famous for several natural springs that run through the town. Local legends claim that the Harding Spring has healing powers, while another, Magnetic Spring, magnetizes any metal dipped into its waters. Visit the Onyx Cave to pan for semi-precious stones, where temperatures stay a cool 60 degrees year-round. It’s a great place to find some relief from the 80-degree-plus temperatures.

07 Florida Keys, Florida

These 700 islands divide the Atlantic Ocean from the Gulf of Mexico and lie just off the southern coast of Florida. They’re home to the only living coral barrier reef. The climate here is similar to that of the Caribbean. September is the wettest month of the year, but daily temperatures seldom dip below 75 at night, and daily highs stay in the upper 80s. Picnic and play volleyball on Higgs Beach and enjoy the Florida sunshine. Cool off in 80-degree waters or jump aboard a catamaran or jet ski to enjoy some at-one-with-the-ocean time.

08 Jackson Hole, Wyoming

A majestic mountain range watches over the town of Jackson Hole, and the area is teeming with wildlife, one of the last examples of America’s Old West. There are two national parks here, the Grand Teton National Park, and just two hours down the road, Yellowstone National Park. Enjoy white water rafting and scenic raft trips until mid-September, when the weather gets much cooler. Expect high temperatures of around 70 degrees until the end of the month, when they start to dip into the upper 50s.

09 Chicago, Illinois

The Windy City has several must-see attractions, and in September, you won’t experience the normally heavy crowds that generally take them over. Visit the visual splendor of Millennium Park and its Cloud Gate sculpture. Experience famous events like the Chicago Jazz Festival or make plans to attend the city’s annual three-day Oktoberfest celebration in early September. Temperatures range from the upper 70s into the low 80s this time of year, so the weather is near-perfect.

10 Buffalo, New York

Art lovers have discovered the city’s new visual arts scene, including a Native American-owned gallery dedicated solely to Indigenous art. Explore the street murals popping up around the city, a joint project between businesses, community groups, block clubs, and artists. Buffalo is just 20 miles from Niagara Falls. Closer to the city, visitors can also enjoy outdoor recreation. Go fishing or swim at Orchard Park or take a walk in the sunshine or kayak at Outer Harbor.

11 Deer Isle, Maine

Couples seeking some alone time or artists looking for inspiration should plan a getaway to Deer Isle, a rural, picturesque cluster of communities on the eastern side of Penobscot Bay in Maine. John Steinbeck featured the town of Deer Isle in his 1962 travelogue, “Travels With Charley In Search of America,” saying it had a “strangeness” to it. The temperatures in September are comfortable, hovering in the mid-70s. View the island’s eight historical lighthouses on a hike along the Deer Isle Lighthouse Trail or explore the moss-covered, shadowy forests of the Barred Island Preserve.

12 Pigeon Forge, Tennessee

Dollywood, Outdoor Gravity Park, and the Titanic Museum are just a few of the attractions in this family-friendly destination in Tennessee. Temperatures steadily decrease through September, but the weather is pleasant and ideal for outdoor recreation. Enjoy a huge array of Southern culinary, cultural, and historical experiences in this popular Smokey Mountain tourist destination.

13 Providence, Rhode Island

Travelers seeking small-town charm combined with big-city amenities will find everything they need in Providence. The vibrant city has an outstanding and respected culinary scene, diverse neighborhoods, a thriving arts community, and an excellent selection of lodging choices. City planners revitalized the downtown area, creating a four-acre green space, Waterplace Park. The weather averages a pleasant 70-degrees in September.

14 Hill Country, Texas

With more than 20 towns to explore, the Texas Hill Country region is made up of some of the most beautiful and interesting destinations in the state. Weather-wise, the best time to visit begins in mid-to-late September when both the humidity levels and the temperatures are cooler. Though larger cities like Austin and San Antonio are included in the Hill Country, it’s the smaller communities like Fredericksburg, Kerrville, New Braunfels, Medina, and others where you experience the diversity and true flavors of the region.

15 Tulsa, Oklahoma

As September rolls in, the temperatures in Tulsa fall by as much as 11 degrees; this city has undergone both physical and cultural changes in recent years, ushering in an updated identity by reconciling with its past. Tulsa thrives on entertainment, trendy eateries, and exclusive boutiques, from art-deco architecture to major performing arts venues. For outdoor fun, visit The Gathering Place, a new green space for people of all ages.


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