Best Places to Visit in September & Things to Do
No matter where the destination is, September is typically a turning of seasons, and that alone offers a unique experience when exploring a new area.
“This might be my favorite month,” I thought, heading to the airport. With kids back in school, I knew that my flight would be quieter than over the summer. In most places, the weather is still warm enough to enjoy the outdoors. If you are hunting for budget options, you can look forward to good deals on hotels and flights to most destinations in September, after Labor Day. These U.S. destinations all offer something unique that I always look forward to.
Best Places to Visit in September:
Poulsbo, Washington: Nordic Charm & Waterfront Calm
“This feels like a fairytale with a ferry schedule,” I thought as I explored Downtown Poulsbo. The town is located along Liberty Bay in Washington, about an hour and a half from Seattle.
The 12-foot Viking statue on Viking Avenue reminded everyone of its Norwegian heritage. I liked the crisp morning air and days that got warmer in the afternoon.
I spent some time at the Port of Poulsbo, walking at Liberty Bay Waterfront Park and relaxing with a view. On an earlier trip, I visited SEA Discovery Center with my kid (free admission). He found their interactive exhibits showcasing the local underwater ecosystems fascinating.
What I Loved Most: Watching the tide come in while sipping coffee on a bench by the marina. I could hear and see seagulls circling above the town.
My highlights? Breakfast at Sluys Poulsbo Bakery. I had a glazed cardamom twist with coffee to start my day.
Plan your September getaway:
- Drive Time from Seattle: ~1.5 hours (including ferry ride)
- Vibe: Relaxed, great for walkers
- Highlights: Liberty Bay Marina, SEA Discovery Center, boutique shopping, Viking heritage
- Best Time to Visit: Mid-September for sunny afternoons and smaller crowds
- Cost: About $15 for the ferry from Seattle (round-trip), Bakery treats and coffee $7, hotels from $119
- Hours: Most shops and cafés open 9am–5pm; the bakery opens at 6am
- Local tip: If you are still in town during the first weekend in October, join the Poulsbo Octoberfest Beer Run ($60) which is very fun
For more ideas nearby, check out my article on day trips from Seattle.
Rapid City, South Dakota: Stone Faces & Prairie Skies
Our flight landed in Rapid City (5 hours, $269 from Austin, TX). We were on our way to see Mount Rushmore (30 minute drive).
“This is where the landscape starts to feel epic,” I thought, looking out over the Black Hills as the sun caught the tops of pine trees.
In September, the air was dry and clear in Rapid City, the light golden. I enjoyed going down the streets full of art, something unique and surprising waiting as I rounded a corner.
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.
My highlights? Lunch at Tally’s Silver Spoon . I had a bison burger with truffle aioli and crispy shoestring fries. The meat was rich and smoky. We ate under a string lights on the patio.
We checked into a motel room at Canyon Lake Resort on the west shore of Canyon Lake in Rapid City. It was quiet and affordable in early September ($122/night).
Plan your September vacation:
- Drive Time to Mount Rushmore: ~30 minutes
- Vibe: Rugged, artistic, quietly bold
- Highlights: Main Street Square, Chapel in the Hills, Custer State Park, Badlands day trips
- Best Time to Visit: September for cool mornings, golden light, and peak hiking weather
- Cost: State park entrance ~$20/car; meals moderate
- Hours: Parks dawn to dusk; restaurants 8am–9pm
Dothan, Alabama: Peanuts, Porches & Southern Ease
I caught a very early morning flight from Austin to Dothan (5 hours with a stop in Atlanta, from $357). We rented a car at Dothan Regional Airport and headed to town for lunch.
“This town smells like warm sugar and grass,” I thought as we walked beneath oak trees just starting to drop their leaves.
Dothan felt like a hometown...even if it wasn’t mine. In September, the heat softened and the sidewalks stayed quiet enough for a romantic stroll.
I spent some time at the Wiregrass Museum of Art learning about acclaimed Alabama artists.
What I Enjoyed: I liked discovering all the murals of farmers, musicians and fields.
My highlights? Breakfast at Blue Plate next morning. I had buttermilk biscuits with country sausage gravy, scrambled eggs, and a side of cheese grits. Everything smelled like butter and bacon from the moment I walked in.
I got a room at Best Western Dothan Inn & Suites ($95) to collect rewards points. The outdoor pool was a plus. Most hotels in towns had rooms available in September.
Plan your September vacation:
- Drive Time from Montgomery: ~2 hours southeast
- Vibe: Friendly, rooted, full of small surprises
- Highlights: Downtown murals, Landmark Park, Wiregrass Museum of Art, peanut stands
- Best Time to Visit: September for pre-festival buzz and lighter crowds
- Cost: Free murals; parks ~$4; meals modest
- Hours: Most attractions 9am–5pm; diners open early
Finding the Rhythm of Fall in Boston
We drove to Boston from NYC in under 4 hours for a quick weekend getaway. September is the perfect time to visit. Summer heat had passed and the students had returned. I could see the leaves begin turning for the fall foliage season.
I walked along the Freedom Trail and thought, “I like Boston's historic vibe and open spaces.”
Crisp evenings on the harbor were magical. I also liked sampling coffee in Beacon Hill and visiting bookstores.
My highlights? Lunch at Neptune Oyster in the North End. I had a buttery lobster roll with lemon aioli. The bustle of the tiny restaurant matched the hum of the city.
A downside? September is a popular time to visit Boston so rooms are very expensive. If you need a central location, Maverick Suites at 40 Temple St is a hidden gem that is about 40% cheaper than most hotels.
Plan your September trip to Boston:
- Drive Time from Providence: ~1.5 hours north
- Vibe: Scholarly, crisp, storied
- Highlights: Freedom Trail, Fenway Park, public gardens
- Best Time to Visit: Mid to late September for early foliage and mild weather
- Cost: Free trails; museums and meals extra
- Hours: Sites open 9am–6pm; city strolls all day
Lebanon, Tennessee: Trains, Antiques & Porch-Swing Pace
A 2 hour 10 minute flight from Austin (from $127) took us to Nashville. We rented a car and drove about 35 minutes to Lebanon, TN, a hidden gem with a lot of southern charm.
“This town feels like it remembers everything,” I thought, standing outside the old train station, It looked polished and welcoming under early September sun.
Lebanon had a slow, sincere, southern vibe that was easy to get used to. The air was still warm, but the light had shifted in September.
I enjoyed poking through antique shops downtown. I caught a scent of flowers from the corner market.
Lunch was at Snow White Drive-In. I had a griddled burger with onions and pickles, served with hand-cut fries and a thick banana shake that I couldn't finish. We ate at a shaded picnic table, cicadas humming just like where I live in Texas.
We stayed at the Cedar Grove Inn ($158/night) and relaxed outdoors by the pool.
Plan your September Lebanon visit:
- Drive Time from Nashville: ~35 minutes east
- Vibe: Small-town warmth with vintage character
- Highlights: Historic train station, antique stores, Cedars of Lebanon State Park, classic diners
- Best Time to Visit: September for festivals, mild weather, and fewer crowds
- Cost: Park free; meals and shops modest
- Hours: Most shops 10am–5pm; diners open 11am–8pm
Antioch, California: Delta Days & Golden Hills
“This is where summer lingers just a little longer,” I thought, watching sunlight ripple over the San Joaquin River. Antioch in September had a dusty shimmer to it, with dry grass glowing on the hills. I saw water lapping gently at marina docks. Warm air was scented with eucalyptus.
What I Loved Most: Walking along the trails at Black Diamond Mines in the cooler morning hourss.
My highlights? A late lunch at Rivertown Sweets. I had a turkey and avocado sandwich on sourdough, followed by a warm apple hand pie. I ate slowly at a shaded sidewalk table. A breeze stirred the napkin in my lap.
Plan your September visit:
- Drive Time from San Francisco: ~1.5 hours east
- Vibe: Laid-back delta town with open skies
- Highlights: Black Diamond Mines trails, Dow Wetlands Preserve, Antioch Marina, Rivertown district
- Best Time to Visit: September for mild breezes, quiet parks, and golden hills
- Cost: Trails and parks free or $5; bakery meals under $15
- Hours: Trails open sunrise to sunset; cafés 10am–4pm
Browse more weekend getaways from San Francisco.
Beverly, Massachusetts: Seaside Quiet & Small-Town Grace
From Boston, we drove about 45 minutes north along the coast to Beverly. “This feels like the kind of place that knows how to exhale,” I thought, standing along the harbor. I watched as seagulls drifted overhead and sailboats rocked gently in the breeze.
In September, Beverly moved at the rhythm of waves. The beaches were only half-full, much quieter than in the summer.
What I Loved Most: Sitting at Lynch Park with my feet in the grass. Clouds drifted past and the sun dipped low behind a rocky bluff.
We didn't spend the night, but if we did I would have booked a room at The Beverly ($256).
One 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.
Plan your September weekend getaway:
- Drive Time from Boston: ~45 minutes north
- Vibe: New England seaside with a local heart
- Highlights: Lynch Park, beaches, Beverly Farmers Market, galleries and gardens
- Best Time to Visit: September for warm afternoons and uncrowded coastal walks
- Cost: Parks and beaches free or $10 parking; meals are affordable
- Hours: Parks dawn to dusk; cafés 8am–3pm
Middletown Flow & September Gold
“This feels like a town tucked between summer and something quieter.” That’s what I thought walking along the Connecticut River, early September light flickering through the trees.
I started the day with a slow walk on the riverfront trail near Harbor Park. The breeze was cool, not cold, just enough to make the leaves whisper. Rowers moved past silently, their oars cutting clean lines into the water. The town felt balanced, like it hadn’t rushed into fall just yet.
One downside? On cold winter evenings, Main Street can feel almost deserted so plan your visit in the spring, summer or fall. September is definitely the way to go.
What I Enjoyed: You can see students from Wesleyan University spilling out of coffee shops.
My highlights? Lunch at a café near Wesleyan: a warm grain bowl with roasted squash, chickpeas, and garlicky tahini dressing. The spices lingered in the air, cumin, cinnamon, something earthy. I ate slowly, watching students drift in and out, notebooks and laughter in tow. Afterward, I wandered campus and found a quiet bench between two buildings overgrown with ivy. I sat down and thought, “This is the kind of day that doesn't need anything added.”
Plan your Middletown day trip:
- Drive Time from: Hartford ~35 min; NYC ~2 hrs
- Vibe: Academic, river-centered, peaceful with a pulse
- Highlights: Harbor Park, Connecticut River trail, Wesleyan University, Main Street cafés
- Best Time: September for crisp mornings, warm afternoons, and fewer crowds
- Cost: Lunch ~$12–18; trails and campus strolls are free; parking metered or low-cost lots
Pittsburgh’s Bridges & Garden Wonders
We arrived in September, the air just cool enough to hint at autumn. From the moment we crossed the first bright yellow bridge, I felt like we’d stepped into a city built for exploring. Hills rose and fell around us, three rivers twisting through neighborhoods like ribbons. “This is going to surprise us,” I thought, and it did.
What I Loved Most: Watching my child dart ahead through the glass pavilions of Phipps Conservatory, pausing to point at bright orchids and giant ferns. The warm, sweet air carried the scent of tropical blooms, while outside, leaves along the paths had just begun to turn gold.
My highlights? Lunch at The Porch at Schenley, with a table overlooking the park. My roasted vegetable flatbread came out hot, rosemary and caramelized onions scenting the air. My child enjoyed a wood-fired pizza, stopping only to watch squirrels chasing each other outside the windows.
Plan your Pittsburgh family day trip:
- Travel Time from Philadelphia: ~5 hours by car; best as an overnight trip with kids
- Vibe: Playful, welcoming, and full of discoveries
- Highlights: Phipps Conservatory, Carnegie Science Center, Pittsburgh Zoo & Aquarium, Duquesne Incline
- Best Time to Visit: Spring and summer for gardens in bloom; September and October for mild weather and colorful hillsides
- Cost: Phipps ~$19 adults, ~$12 children; many attractions offer family passes
- Hours: Most attractions open 10am–5pm; check seasonal schedules
September Wrap-Up: The Quiet Glow Between Seasons
By the time the last stop faded in the rearview mirror, I thought, “That’s how to end a summer.” September had slipped by gently, no loud hellos, no dramatic goodbyes. Just the steady, golden rhythm of places that knew how to slow down without stopping. These towns and trails offered space to breathe, to notice, and to eat well while the world softened at the edges.
What I Loved Most: The in-between feeling, warm days, cool mornings, fewer crowds, and time to wander without checking the time. It felt like a deep breath held just before autumn exhales.
My highlights? Sitting outside wherever I could, a warm pastry or sandwich in hand, breeze on my arms, and that early fall light turning sidewalks and harbors into quiet poems. Every place gave me something different, but they all reminded me that September isn’t the end of summer, it’s its softest note.
Plan your next September getaway:
- Best For: Travelers who crave calm, crisp air, and uncrowded places
- What to Pack: Layers, a good book, sturdy shoes, and a sense of stillness
- Why It Works: It’s the sweet spot, before the rush, after the heat, when everything opens up
