10 of the Coolest Places to Visit in September
September is one of the best months to travel in the United States, with cooler weather, fewer crowds, and plenty of seasonal events and outdoor activities. From coastal escapes and mountain getaways to vibrant cities and charming small towns, September offers the perfect balance of relaxation and adventure.
I’ve enjoyed crisp mornings hiking scenic trails, wandered through lively harvest festivals, and taken trips where the summer crowds had faded but the beauty remained in full swing. Whether you’re looking for a romantic getaway, a family trip, or a solo adventure, there are countless places to visit and things to do across the U.S. in September. Here are the ones I recommend, and I think you’ll enjoy them too.
1. Poulsbo, Washington
I loved visiting this charming coastal town during September, as it turned out to be one of the sunniest times of the year.
The weather was pleasantly warm, perfect for kayaking in Liberty Bay, strolling the historic downtown, boat tours during the whale-watching season, and hiking trails in the fall.
The town truly came alive with community events and festivals, including the Poulsbo Artwalk and Poulsbrew.
I drove about an hour and a half from Seattle, and my getaway lasted two delightful days from my comfy base at Poulsbo Inn & Suites.
It was a gorgeous weekend filled with kayaking in Liberty Bay at sunrise, hiking forested trails nearby, whale watching in the Puget Sound, and savoring al-fresco dinners along the waterfront. Between the coastal beauty, Scandinavian heritage, and vibrant September events, Poulsbo charmed me completely. I have to say that if you are not ready for it, a sudden rain shower can be uncomfortable.
My favorite highlights: Spotting orcas and humpbacks in the Puget Sound made the trip unforgettable.
2. Rapid City, South Dakota
Visiting Rapid City in September turned out to be a wonderful choice, with clear skies and some of the most enjoyable weather of the year.
The mild temperatures made it ideal for venturing into Badlands National Park, wandering through the city’s downtown, cruising the scenic highways of the Black Hills, and hiking the colorful trails of Custer State Park.
The city had a lively energy, thanks to seasonal gatherings. Attending the Great Downtown Pumpkin Festival with my son was very fun.
Flying into Rapid City Regional Airport was simple (we caught a 20-minute shuttle into town), and from there I set out on a two-day adventure. We spent two nights at Canyon Lake Resort. The city made the perfect home base, with both Mount Rushmore and the surrounding parks just a short drive away. I’d recommend bringing layers since the Black Hills weather can shift quickly.
My most surprising find: I drove around the 18-mile loop through Custer State Park and saw buffalo and hawks. It took about 2 hours. You can also go on a guided tour ($329) if you prefer.
3. Dothan, Alabama
I took a break to visit Dothan, Alabama this month and found the weather warm and sunny. The city was buzzing with events, including the lively National Peanut Festival and Downtown Dothan’s First Friday Art Walk
I drove down from Montgomery in just under two hours and stayed at the Best Western Dothan Inn & Suites for to nights.
I spent my vacation visiting the Dothan Area Botanical Gardens, exploring the Forever Wild Trails at Beaver Creek, kayaking on the nearby Choctawhatchee River, tasting craft brews at Folklore Brewing & Meadery, and wandering through the city’s famous Peanut Around Town sculptures scattered across its historic downtown.
Highlight of my trip: Relaxing in the gardens at Landmark Park, a living history park that also preserves Alabama’s natural beauty.
4. Lebanon, Tennessee
I took a break to Lebanon, Tennessee this month and found the weather warm and inviting – perfect for strolling around historic downtown, exploring lush green parks, and enjoying the relaxed pace of this charming Southern town. The atmosphere was full of small-town friendliness, summer blooms brightened the streets, and there was a laid-back country vibe all around.
I also loved that the area was buzzing with events – the Wilson County Fair – Tennessee State Fair brought rides, concerts, and delicious fair food, while local farmers markets offered everything from fresh produce to handmade crafts. The downtown square often comes alive with music, art walks, and community gatherings that make Lebanon feel both lively and welcoming.
I drove just 30 minutes from Nashville and stayed at the comfortable Cedar Grove Inn for a few days. During my trip, I explored the historic Lebanon Town Square, walked the trails at Cedars of Lebanon State Park, browsed antique shops and local boutiques, tried homestyle Southern cooking at Sunset Restaurant, and discovered the town’s railroad heritage at the Lebanon Train Station Museum.
Highlight of my trip: Tasting Southern comfort food – fried catfish and cornbread at a family-run diner hit the spot after a day of exploring.
5. Antioch, California
I took BART’s Yellow Line to Antioch (about 1 hour 10 minutes from Oakland, $6.70 one way). It was a perfect day trip and I didn't spend the night.
I found the weather sunny and warm in Antioch, perfect for exploring the waterfront, hiking local trails, and taking in the relaxed Bay Area vibe. With the golden hills as a backdrop, breezes off the San Joaquin River, and plenty of sunshine, it was a refreshing and easygoing escape.
I also loved that the city and surrounding region were alive with events, from concerts at the El Campanil Theatre to the bustling Antioch Summer Farmers Market, and community celebrations along the historic waterfront. Being so close to wine country and the Delta, there were also seasonal festivals highlighting food, music, and culture.
During my trip, I wandered along the Antioch Marina and Waterfront District, checked out Black Diamond Mines Regional Preserve, watched kayakers on the San Joaquin River Delta, and browsed the shops and murals downtown.
Looking for more local ideas? Browse more weekend getaways from San Francisco.
6. Beverly, Massachusetts
September weather in Beverly was perfect for strolling along the North Shore beaches, wandering through leafy neighborhoods, and enjoying the easy coastal New England vibe. With sailboats dotting the harbor, historic streets lined with flowers, and a laid-back seaside atmosphere, it felt like a charming and relaxing escape.
I checked out the Lynch Park Harbor Fest and I appreciated that it was free to attend.
We drove just 45 minutes from Boston and stayed at The Beverly for a long weekend. During my trip, I relaxed on the sandy shore of Dane Street Beach, explored the scenic trails at Lynch Park, discovered Beverly’s maritime past at the Historic Beverly Cabot House, sipped coffee at cozy downtown cafés, and took in sweeping ocean views along the coastline of Beverly Farms.
Everything was great except I found that Cabot Street, lively with cafés and theaters, can also feel cramped with traffic during rush hour, even in the off season.
7. Middletown
Middletown, Connecticut weather this month is warm and pleasant, perfect for strolling along the Connecticut River, exploring historic streets, and enjoying the blend of small-town charm with a lively college-town energy. The summer flowers brightened up Main Street, and the whole town had a welcoming, easygoing vibe.
I also loved that Middletown was alive with events such as open mic nights, outdoor family storytime and more.
I drove just 30 minutes from Hartford and stayed at the cozy Inn at Middletown, a historic boutique hotel right on Main Street. During my trip, I enjoyed the peaceful Harbor Park along the riverfront, wandered the beautiful grounds of the Wadsworth Mansion at Long Hill Estate, explored art exhibitions at Wesleyan University’s Center for the Arts, dined at farm-to-table restaurants like O’Rourke’s Diner and Roux, and browsed the eclectic shops downtown.
Highlight of my trip:. Enjoying live music downtown – the energy of local festivals and concerts gave the city a wonderful sense of community
8. Pittsburgh
I drove 4 hours west from Philadelphia into Pittsburgh, where the Allegheny, Monongahela, and Ohio Rivers meet.
September in Pittsburgh is one of my favorite times to visit because the city feels vibrant, cool, and full of energy without the heavy summer crowds.
The weather is mild, the leaves just begin to change, and every corner of the city offers something exciting and unique.
I also loved that the city was alive with events like the Pittsburgh Renaissance Festival and the Pittsburgh International Jazz Festival. I really enjoyed being able to attend, but I noticed hotel prices in the area were steap.
Chris and I stayed at the stylish Kimpton Hotel Monaco Pittsburgh, right in the heart of downtown. During my week, I wandered through the vibrant Strip District for food and markets, admired the masterpieces at the Carnegie Museum of Art, kayaked along the Three Rivers Water Trail, and soaked up the cozy atmosphere of local breweries and coffee shops in Lawrenceville.
My absolute favorite here was the Duquesne Incline for sweeping city views!
9. Boston
September in Boston is honestly one of my favorite times to visit. When my husband and I were based on the East Coast, we always spent at least one night in Boston this time of year.
The weather mild and breezy, perfect for walking along the city’s historic streets, exploring leafy parks, and soaking up the coastal views along Boston Harbor. With flowers brightening the public gardens and a lively urban buzz in the air, it felt like the ideal mix of history, culture, and modern energy.
I also loved that the city was brimming with events that made the city feel festive and full of life. Boston's SoWa Open Market was in full swing, along with the annual Boston Arts Festival.
We drove up from New York in about four hours and stayed at Maverick Suites at 40 Temple St. During my week in Boston, I strolled along the Freedom Trail, relaxed in the Boston Public Garden, took a ferry to the Boston Harbor Islands, sampled craft beer at Harpoon Brewery, and spent an afternoon wandering through the collections at the Museum of Fine Arts.
Highlight of my trip: Dining in the North End, Boston’s Italian district. A plate of handmade pasta at Giacomo’s was unforgettable, and the cannoli from Mike’s Pastry was the perfect sweet ending.
10. Mauna Lani, Big Island of Hawaii
When I lived on the Big Island of Hawaii, September was my number one month for relaxation. Summer crowds were gone which meant that we had the beaches all to ourselves. With vibrant tropical flowers blooming everywhere and gentle trade winds carrying the scent of plumeria, it felt like pure island paradise.
The Mauna Lani resort area was full of culture and events, from Hawaiian music and hula performances at sunset to local craft markets, and even traditional ceremonies that celebrate the Big Island’s heritage. There’s such a seamless blend here of luxury, relaxation, and authentic Hawaiian traditions.
For a splurge, I recommend the Fairmont Orchid for a long weekend. You can get a massage over the waterfall at their super cool spa, relax with a view of the waters of Makaiwa Bay, swim with colorful reef fish and graceful sea turtles (you can rent the gear, so don't overpack!).
At sunset, my husband, son and I went for walks around the historic Kalahuipua‘a Fishponds before heading to dinner. I really cherished this time with my son while he was still little and didn't have to go to school in September.
My favorite experience was snorkeling with Hawaiian green sea turtles at Makaiwa Bay.
Conclusion
Looking back on all these September adventures I can honestly say that this month is one of the absolute best times to travel.
Each place has its own unique magic in early fall. The weather is crisp, the crowds are smaller, and every destination feels more joyful, affordable, and welcoming.
For me, these places prove that September is the dream travel month. Trust me, you’ll find magic waiting in the most unexpected corners.
Try one of these vacations next:
Booking Checklist
1. Book Your Flight - I use Expedia because I like their mobile app with my itinerary. They've helped me re-book flights on many occasions. Once you reach their Gold tier, support is especially good.
2. Book Your Hotel - I use Booking.com or Expedia, depending on my destination.
3. Book Your Rental Car - I use Expedia.
4. Book your tours on Viator or Get Your Guide.
