Places to Visit in September
I think that September is one of the best months for a road trip, especially after Labor Day weekend. Why? You can look forward to cooler weather, fewer crowds, and plenty of seasonal events. In some places up north, you'll see leaves starting to turn golden and red too. Here are the the places we've loved visiting, and I hope you’ll enjoy them too.
New Orleans
I fell hard for New Orleans and ever since it's been one of my favorite late summer destinations since moving to the South. Moreover, not counting Mardi Gras in February, I think that September is the best time to visit the Big Easy. Why? Temperature starts to inch lower and it's not nearly as rainy as August.
I find it enjoyable to just stroll around town in the morning, followed by a nice Southern lunch. During the hotter afternoons, I visit New Orleans Museum of Art or the Museum of Illusions with my son. I love going out for a late dinner and sitting outdoors on a patio to end the day.
Rapid City, South Dakota
There are heaps of unique things to do here and visiting Rapid City, South Dakota in September turned out to be the best idea!
The mild temperatures made it ideal for venturing into Badlands National Park, exploring the city’s downtown, cruising the scenic highways of the Black Hills, and hiking in Custer State Park.
The city had a lively energy too, 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 from the airport. I loved that the city made the perfect home base, with both Mount Rushmore and the surrounding parks just a short drive away. I have to warn you, though, that parking can be a challenge! I recommend picking a hotel that offers easy parking.
- Average September temperature (Rapid City, SD): 46.7 °F – 76.6 °F (8.2 °C – 24.8 °C)
My most surprising find: I drove around the 18-mile loop through Custer State Park and saw buffalo and hawks. It took about two hours. You can also go on a tour with a local guide ($329).
A downside? I’d recommend bringing layers since the Black Hills weather can shift quickly in September.
Dothan, Alabama
I thought this was one of the best places to visit in September in Alabama when I moved to the South. Why? I loved that 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 to "Circle City" in just under two hours over the weekend. I instantly thought our journey was worth it!
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 across its historic downtown.
- Average September temperature (Dothan, AL): 69.6°F – 86.9°F (20.9°C – 30.5°C)
Highlight of my road trip: Relaxing in the gardens at Landmark Park was my personal highlight, a living history park that also preserves Alabama’s natural beauty.
We stayed at the Best Western Dothan Inn & Suites (from $102/night) for two nights
Tulsa
This place surprised me with its attractions and green parks. Looking for a cool September destination in the Midwest? Head to Tulsa, one of my favorite places when I'm in the mood for live music and world-class museums.
You'll find Tulsa on the banks of the Arkansas River. First, I recommend exploring the walkable arts districts. Enjoy the stunning Philbrook Museumof Art, and stroll along the Gathering Place riverfront park.
When you get hungry, don't miss KEO Asian Cuisine. It has a unique take on Southeast Asian cuisine that's very tasty.
In the evening, choose from jazz clubs and big-name concerts at the BOK Center.
From OKC we headed to Tulsa, an hour and 40 minutes away. We checked into the stylish Hyatt Regency Tulsa Downtown for three days.
What I loved best:
Browsing vintage shops and stopping for coffee in the bohemian Cherry Street area was my personal highlight.
Lebanon, Tennessee
I fell hard for Lebanon, home to approximately 51,500 people. I found the weather perfect for strolling around historic downtown, exploring lush green parks, and enjoying the relaxed pace of this charming Southern town.
This is my favorite time to visit Tennessee because September brings that gentle shift toward fall without yet losing the warmth of the summer.
I also loved that the area was buzzing with events – Tennessee State Fair brought rides, concerts, and delicious fair food, while local farmers markets offered everything from fresh produce to handmade crafts.
I drove just 30 minutes from Nashville and stayed for five care-free days. During my trip, I explored the historic Lebanon Town Square, walked along the trails at Cedars of Lebanon State Park, and browsed antique shops and local boutiques.
- Average September temperature (Lebanon, TN): 61.5 °F – 81 °F (16.4 °C – 27.2 °C)
Highlight of my trip: Tasting Southern comfort food at Town Square Social where dry rubbed wings were my personal highlight.
Antioch, California
I thought this city of approximately 115,000 people was an absolute gem! It quickly became one of my favorite places for a romantic Northern California weekend. Why? First off, Antioch has that classic East Bay energy without the hurry. In addition, we loved exploring the waterfront, and hiking on local trails.
We took BART’s Yellow Line to Antioch (about 1 hour 10 minutes from Oakland, $6.70 one way). I though that it was the perfect Bay Area day trip in September!
I especially love visiting Antioch Summer Farmers Market where we picked up snacks. Afterwards, we wandered along the Antioch Marina and Waterfront District.
- Average September temperature (Antioch, CA): 57.7 °F – 85.3 °F (14.3 °C – 29.6 °C)
What I loved best:
Hiking in Black Diamond Mines Regional Preserve with Chris was my personal highlight.
Looking for more local ideas? Browse more weekend getaways from San Francisco.
Beverly, Massachusetts
This place completely wowed me! What I love most about this town is how quickly it opens into beautifully untouched coastal scenery.
September weather here was perfect for admiring the view from 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, this was a charming and relaxing escape that completely won me over.
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 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, and took in sweeping ocean views along the coastline of Beverly Farms.
- Location: In northeastern Massachusetts on the North Shore, along the Atlantic coast just north of Salem
- Average September temperature: 57.7 °F – 71.1 °F (14.3 °C – 21.7 °C)
What I loved best:
Sipping warm coffee at cozy Atomic Cafe was my personal highlight.
A downside? I found that Cabot Street, lively with cafés and theaters, can also feel cramped with traffic during rush hour, even in the off season.
Middletown, Connecticut
I thought this city of approximately 48,000 people was truly special. When we moved to the East Coast, this town quickly became one of my favorite places to escape from NYC, about two hours by car.
The weather this month was warm, perfect for strolling along the Connecticut River, exploring historic streets, and enjoying a lively college-town energy on our road trip. I loved the way the summer flowers brightened up Main Street in September.
I also loved that Middletown was alive with events such as open mic nights, outdoor family storytime and more.
During my trip, I enjoyed the peaceful Harbor Park along the riverfront, visited the beautiful grounds of the Wadsworth Mansion at Long Hill Estate, and explored art exhibitions at Wesleyan University’s Center for the Arts.
- Average September temperature (Middletown, CT): 56°F – 74°F (13.5°C – 23.1°C)
Highlight of my trip:. Enjoying live music downtown was my favorite highlight. I loved the energy of local festivals and concerts that gave the city a wonderful sense of community in September!
Pittsburgh
I was in awe of Pittsburgh and everything it had to offer. I especially loved spending time here in September because the whole experience felt inviting 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 drove 4 hours west from Philadelphia into Pittsburgh, where the Allegheny, Monongahela, and Ohio Rivers meet.
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.
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. I toured the fascinating Phipps Conservatory and Botanical Gardens which was my personal highlight with beautiful fall foliage colors or reds, browns and gold.
- Location: In southwestern Pennsylvania at the junction of the Allegheny, Monongahela, and Ohio Rivers, east of the Ohio border
- Average September temperature (Pittsburgh, PA): 55.9°F – 75.7°F (13.3°C – 24.3°C)
My absolute favorite here was the Duquesne Incline for sweeping city views!
Chris and I stayed at the stylish Kimpton Hotel Monaco Pittsburgh, right in the heart of downtown.
Barbialla Nuova, Italy
I thought that this place was one of the most scenic spots in Europe. Ready for a September trip to Tuscany? Whether you love history or simply beautiful nature, this is my favorite time for a trip to Italy. During my year living in Florence, I discovered 3-star Barbialla Nuova (Google Maps pin), a spectacular organic farm-estate. You'll find it in the rolling hills of Tuscany, just over an hour from Florence.
I instantly fell for the eco-friendly vibe of the estate. You'll be accommodated in a restored farmhouse with stone walls and wooden beams, like something out of a movie. It's absolutely perfect for an anniversary vacation.
I woke up to the most amazing sunrise views over vineyards and olive groves, and I honestly thought it was like stepping into a dream. The weather was still warm in September, perfect for enjoying outdoors. It was also olive harvest season.
What I loved best:
I especially loved the cooking classes, where I learned to make fresh pasta, and taste truffles right from the land.
For even more variety, you can visit so many cool sights nearby, including Tempio Di Minerva Medica Montefoscoli, Gambassi Terme, Livorno and Florence.
Mauna Lani, Big Island of Hawaii
I thought that this place was like no other on the planet. When Chris, our son and I lived in Hawaii, September was my absolute favorite month for relaxation. Once summer crowds were gone after Labor Day, we had the beaches all to ourselves. It felt like pure island paradise. If you can get away to Hawaii in September, I know you will love it.
The Mauna Lani resort offered Hawaiian music and hula performances at sunset. 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. You can rent the gear at the hotel.
At sunset, my husband, son and I usually went for a walk around the historic Kalahuipua‘a Fishponds before dinner. I really cherished this time with my son while he was little and didn't have to go to start school in September.
What I loved best:
For me, Mauna Lani was one of the best places to visit in September because it's relaxing and unique! My favorite experience was snorkeling with Hawaiian green sea turtles at Makaiwa Bay.
