There’s something magical about small towns—the slower pace, the unique charm, and the way they make you feel like you’ve stepped into a postcard.
Maybe it’s the Gilmore Girls effect of romanticizing a place where everyone knows you or maybe it’s just a side effect of getting older, but now that I’m in my 30’s I have really grown to appreciate visiting small towns.
Don’t get me wrong, I am a city girl at heart—but there’s something about a slow stroll in the morning, trying cozy café, popping into a cute shop and trying the local fare.
If you’ve noticed that your Instagram feed is filled with people jetting off on international trips, don’t forget about what is right here in your own backyard!
Over the years, I’ve been lucky enough to explore some of the most beautiful and memorable small towns in America.
From coastal gems to mountain escapes, these places have certainly left a mark on me, and I am excited to round them up for you to explore virtually in today’s post.
Whether you’re planning your next getaway or just daydreaming about travel (me always, lol), these are some of the best small towns in the US to visit in no particular order.
Prepare for the wanderlust to set in.
Hudson, New York
This upstate New York town is a blend of historic charm and modern creativity, with its beautifully preserved architecture and thriving arts scene.
Hudson’s antique shops, farm-to-table restaurants, and views of the Hudson River make it an ideal weekend escape.
Hudson is also easily accessible from NYC by train!
Where to stay:
- If you are willing to splurge, I absolutely must implore you to stay at The Maker Hotel. My mom and I did a night there over the summer and it was worth every penny. I have a whole post about the hotel here if you want to see more photos and learn about our experience.
- If you’re on a bit more of a budget, Andrew and I have also stayed at The Wick, which requires a short walk into the main town but is still a great option!
What to do:
- Truly, just wander Main Street and enjoy. From cafés to clothing boutiques and antique stores you’ll be delighted wondering what you’ll stumble across next as you walk around.
- There are also some awesome breweries and restaurants including the one at The Maker Hotel.
Jackson, Wyoming
Nestled in the heart of the Teton Range, Jackson is a gateway to outdoor adventure and stunning landscapes.
Known for its world-class skiing, vibrant arts scene, and charming town square with iconic elk antler arches, it’s a must-visit for nature lovers, adventure seekers and anyone looking for a unique destination.
Where to stay:
- We chose to do an AirBnB in Jackson because lots of people rent out their homes throughout the year, but there are also a few hotels in the main town.
What to do:
- Enjoy the great outdoors! You’re right next to Grand Teton and Yellowstone—two incredible National Parks.
- Either rent a car and explore on your own or book one of the dozens of tours through each that are offered every day.
- Don’t forget to grab a beer at StillWest Brewery with a view of Snow King mountain ro dance to live music at the Million Dollar Cowboy Bar in the evening.
Hood River, Oregon
Situated along the Columbia River Gorge, Hood River is a haven for outdoor enthusiasts, offering windsurfing, hiking, and cycling opportunities.
The town boasts a welcoming vibe with local breweries, orchards, and stunning views of Mount Hood.
Where to stay:
- We were actually in the area for my cousin’s wedding which was right across the river in White Salmon, Washington!
- We stayed at Hotel Iconica which was a 15 minute drive across the river into Washington state from Hood River.
- If you’re looking for something quiet and you have a car, that’s a great option. However, there are also lots of options in Hood River.
What to do:
- Enjoy the outdoors! Go on a hike or drive up to iconic Mount Hood, explore the nearby lavender farm or grab a seat outside at any number of breweries in the area.
- If you’re extra adventurous, this is one of the best places to windsurf in the country because of the wind tunnel that is created on the river.
- There are also some great local breweries including Full Sail Brewing Company and Ferment Brewing Company.
Monterey, California
Monterey enchants visitors with its historic charm and coastal beauty, highlighted by the world-renowned Monterey Bay Aquarium.
The town’s Cannery Row and scenic 17-Mile Drive make it a perfect mix of natural splendor and cultural heritage.
Where to stay:
- We were in Monterey when Andrew ran the Big Sur Marathon in 2022 and we chose to stay at Hotel Pacific. It was easy to walk around the main part of town and the property was very pretty!
What to do:
- Walk by the waterfront and take in the views! Be sure to stop in at any of the local restaurants—though our favorite was definitely Osteria al Mare which was right on the water.
- You can also drive to nearby Big Sur and Carmel-by-the-Sea. We visited Fieldwork Brewing Company after Andrew ran his race!
Cannon Beach, Oregon
Known for its iconic Haystack Rock, Cannon Beach offers breathtaking coastal views and a serene atmosphere just about an hour’s drive from Portland.
The charming town is filled with art galleries, boutique shops, and cozy cafes, making it a delightful retreat.
Where to stay:
- Admittedly, we were staying in Portland when we visited Cannon Beach so we only made it out for the day!
- The drive from Portland is actually incredible—the pine trees were so large as we got closer to the coast and it felt like driving through a postcard.
- However, staying anywhere within walking distance from the beach would make for a great home base during your visit.
What to do:
- Take a walk on the beach! Seeing Haystack Rock in person is truly beautiful. We also grabbed lunch at Pelican Brewing where I ordered the mussels and enjoyed a craft beer.
Beacon, New York
Nestled along the Hudson River, Beacon is a vibrant town known for its thriving arts scene and creative energy.
From the renowned Dia:Beacon contemporary art museum to its charming Main Street filled with boutiques and cafes, this town is a perfect blend of culture and small-town charm.
Beacon is also easily accessible from NYC by train!
Where to stay:
- The Roundhouse Hotel lies at the edge of Main Street in Beacon and is a beautiful hotel (they do weddings here!) and it’s quieter than I staying in the main strip would be.
What to do:
Boulder, Colorado
Nestled at the foot of the Rockies, Boulder is renowned for its stunning mountain scenery and active outdoor lifestyle.
Pearl Street Mall, filled with shops and restaurants, adds to the charm of this vibrant and eco-conscious town.
Where to stay:
- We’ve actually stayed at Hotel Boulderado twice now and we love this historic hotel that is just a few streets away from the Pearl Street Mall and the center of town in Boulder.
What to do:
- In Boulder we typically try to go for a hike up in the Flatirons and spend the afternoon wandering Pearl Street and checking out the local craft beer scene and restaurants.
Greenport, New York
Located on Long Island’s North Fork, Greenport is a charming maritime town known for its waterfront views, fresh seafood, and quaint boutiques.
Its proximity to vineyards and historic sites makes it a favorite summer destination.
Greenport is also easily accessible from NYC by train!
Where to stay:
- The Harbor Front Inn was a great spot for us to stay at in Greenport! It was walkable from the train and the center of town and it even had its own pool.
- Their sister hotel The Sound View also looked great, but it was further out from the town center.
What to do:
- We had a blast just walking around the town. You can also go to 67 Steps beach and one afternoon we chose to bike from our hotel to the Kontokosta Winery for a tasting.
Bolton Landing, New York
Set on the shores of Lake George, Bolton Landing offers a peaceful retreat with breathtaking views of the Adirondacks.
The town’s cozy inns, water activities, and proximity to hiking trails create an idyllic escape.
Where to stay:
- We usually rent an AirBnB or VRBO house here when we go up with Andrew’s family, but we have always wanted to stay at The Sagamore.
What to do:
- It’s all about lake life when you’re by Lake George! If you can, rent a boat on the lake and go swimming.
- Check out some of the local breweries like Bolton Landing Brewing Co. but my favorite evenings by the lake involve hanging at the house, cooking or ordering in food and resting after a day in the sun.
Portsmouth, New Hampshire
This historic seaside town captivates visitors with its cobblestone streets, vibrant arts scene, and waterfront charm.
Portsmouth is rich in colonial history, yet modern with unique shops, breweries, and seafood restaurants.
Where to stay:
- We chose to stay at The Hotel Portsmouth and we absolutely loved it. It’s a historic hotel that is just a short walk from the center of town.
What to do:
- I could spend all day exploring this cute oceanfront town.
- Grab a lobster roll by the water, pop into some of the unique gift shops (here’s looking at you Pickwick’s Mercantile) and grab a local beer from one of the breweries.
- You can even take a day trip to Maine to visit York and see the Nubble Lighthouse or Kennebunkport, which is supposed to be beautiful.
Napa, California
The heart of California’s wine country, Napa is famous for its rolling vineyards, world-class wineries, and exceptional culinary scene.
Its relaxed pace and stunning landscapes make it an ideal destination for wine lovers and foodies.
Where to stay:
- Some people choose to add Napa to their San Francisco itinerary as a day trip, but we really enjoyed staying in the town of Napa at the The Napa Inn & Spa.
- They had unique homemade breakfasts in the morning and one of our wine tours even picked us up right from the hotel.
What to do:
- It’s obvious, isn’t it? Napa is known for the wine and the culinary scene, so sit back and indulge. We did Platypus Wine Tours and the Napa Valley Wine Trolley and loved all of the tastings we were taken to.
- In addition to exploring any number of fabulous wineries, you can also dine at a restaurant like The French Laundry, which has not one, not two, but THREE Michelin stars.
Mystic, Connecticut
Famous for its maritime history and charming harbor, Mystic offers attractions like the Mystic Seaport Museum and Mystic Aquarium.
The town’s quaint streets and delicious seafood make it a quintessential New England destination.
Where to stay:
- We didn’t stay the night in Mystic, but there are lots of local inns and hotel chains in the area.
What to do:
- Walk around this coastal town and pop into local gift shops and bookstores, grab a bite at any number of fun restaurants and sit out and enjoy the view.
- We got coffee and donuts from Young Buns (I think they may have closed or moved) and also had lunch at The Engine Room.
Cape May, New Jersey
Known for its Victorian architecture and pristine beaches, Cape May is a charming seaside resort with a nostalgic feel.
Visitors can enjoy its historic lighthouse, vibrant arts scene, and relaxing coastal vibe.
Where to stay:
- We stayed at an awesome rental property in Cape May called The Gray Owl, which is sadly no longer taking reservations. Otherwise there are plenty of hotels in the area to explore.
What to do:
- Go to the beach, take a day trip out to Beach Plum Farm or Cape May Winery, and be sure to walk along the main street and take a photo by the bell!
Ocracoke, North Carolina
Ocracoke is a 16-mile long island that is only accessible by ferry—it is not the easiest place to get to, but it is absolutely worth the trip.
It has a charming feel and most residents drive golf carts rather than actual cars. It features lots of great restaurants, beaches, and places to relax.
Where to stay:
- The Castle Inn at Silver Lake: we stayed for two nights at this gorgeous historic home. Breakfast was included with our stay and it was walkable to the main part of town.
What to do:
- Go to the beach, spend the afternoon at 1718 brewery, and pick up a coffee from the Ocracoke Coffee Company! (Come back here in the evening when The Mini Bar opens!)
Nantucket, Massachusetts
This small island off the coast of Cape Cod attracts hundreds of thousands of visitors every summer, and it’s easy to see why.
From the homes covered in weathered, cedar shingles to the hydrangeas that bloom and all of the charming cobblestone streets, Nantucket feels like a return to a peaceful life.
Where to stay:
- The Carlisle House Inn: this historic hotel was just a few streets away from dozens of restaurants, museums and attractions, but we loved that it was on a quiet side street.
What to do:
- Pop in and out of the cute shops from Mitchell’s Book Corner to Murrary’s Toggery, have a glass of wine (or two) at Cru, and drive out to Sconset to see some of the most beautiful homes on the island.
More US small towns on my list to visit:
- Asheville, North Carolina (going this month!)
- Stowe, Vermont (we were supposed to go after our wedding for a mini moon but I got the C-word 😭and we had to cancel)
- Marfa, Texas (and specifically the Prada store)
- Sedona, Arizona (another cancelled 2020 trip but I still want to visit here!)
- Kennebunkport, Maine (would be a great late summer/early fall destination for a road trip from NYC)
Now I need to know—what is your favorite small town in the US? Let me know in the comments!
yours,
Austen
