Small Towns for a Family Vacation
Small towns in the United States make wonderful family vacation destinations, offering charm, safety, and plenty of activities without the crowds of big cities. With their welcoming atmospheres, scenic surroundings, and kid-friendly attractions, these towns create the perfect setting for making lasting memories together.
I’ve strolled down quaint main streets lined with local shops, enjoyed festivals and farmers’ markets, and found endless opportunities for outdoor fun. Whether you’re looking for a peaceful retreat, an adventurous getaway, or a little of both, small towns across the country offer something special for families. Here are the ones I recommend, and I think you’ll enjoy them too.
1. Make Waves in Naples, Florida
We drove about 2 hours west from Miami to Naples. Once a 19th-century winter resort for wealthy northerners, it’s still famed for luxury shopping, arts, and white-sand beaches.
We explored Historic Third Street South and Fifth Avenue South, visited the Naples Depot Museum (1927 train station, free), and caught sunset at the Naples Pier (1,000 feet long, rebuilt after hurricanes).
Overnight we stayed at The Escalante, a boutique Mediterranean-style hotel steps from Fifth Avenue with tropical gardens and pool ($285).
When I think of the absolute best family vacation spots, Naples, Florida instantly comes to mind. Nestled on the Gulf of Mexico in Southwest Florida, this small town feels like a hidden gem waiting to be explored.
We had the most amazing time walking along Naples Pier, watching dolphins swim by, and catching one of the most spectacular sunsets I’ve ever seen. It was such a joyful family moment that I’ll never forget.
One of my favorite parts of Naples is how affordable and family-friendly it can be, while still offering luxury experiences if you want them. It feels like a dream mix of relaxation and adventure.
We explored white sandy beaches that felt almost untouched, and my kids thought it was the coolest place to build sandcastles and splash in the calm, clear water. I loved how safe and inviting the vibe was.
What makes Naples especially unique is its vibrant mix of nature and culture. We spent one day at the Naples Botanical Garden, which was both exciting and educational, and another exploring the Naples Zoo—an underrated family attraction that surprised us with its cool wildlife encounters.
Our weekend getaway felt magical because there was something for everyone—kayaking through mangroves, browsing unusual local shops, and enjoying fresh seafood at waterfront restaurants. Every experience felt like a brilliant idea come to life.
For me, Naples is one of the best small-town destinations in Florida, offering an unforgettable family getaway filled with charm, beauty, and a touch of coastal magic.
2. Get Creative in Santa Fe, New Mexico
We drove about 1 hour north from Albuquerque to Santa Fe. Founded in 1610, it’s the oldest state capital in the U.S. and still radiates Pueblo and Spanish Colonial heritage.
We toured the Santa Fe Plaza (a National Historic Landmark, lined with adobe buildings), visited the Georgia O’Keeffe Museum ($20 admission), and browsed the Palace of the Governors’ Native American art market. Overnight we stayed at Inn of the Five Graces, a boutique hotel with adobe casitas decorated in hand-carved wood and vivid textiles ($325).
When we planned a family getaway to Santa Fe, New Mexico, I didn’t expect it to feel so magical. Nestled in the foothills of the Sangre de Cristo Mountains, this small town is one of the coolest and most unique destinations I’ve ever experienced.
We wandered through the vibrant Santa Fe Plaza, filled with artists, street performers, and local vendors—it felt like stepping into a living piece of history. The adobe-style architecture gave everything a warm, unusual charm that instantly became one of my favorite sights.
Our kids thought it was the absolute best when we explored Meow Wolf, an amazing immersive art installation that is both unusual and spectacular. It’s one of those hidden gems that makes Santa Fe so exciting for families.
I loved how affordable and joyful the weekend felt, with endless opportunities to explore galleries, unique shops, and cozy cafés. We also discovered local treasures like the Georgia O’Keeffe Museum, which gave us such an interesting cultural experience.
One of my favorite memories was hiking just outside town in the mountains, where we enjoyed cool pine-scented trails and panoramic views. It was an underrated highlight that made our trip feel like a dream adventure.
We ended our days enjoying delicious New Mexican food—enchiladas smothered in red and green chile sauces were a brilliant idea for dinner after a day of exploring. Every bite was unforgettable.
For me, Santa Fe is one of the best small-town family destinations in the Southwest—colorful, artistic, and absolutely filled with magic.
3. Adventure Together in Asheville, North Carolina
We drove about 2 hours west from Charlotte to Asheville, tucked into the Blue Ridge Mountains. Known for its Art Deco downtown and bohemian flair, Asheville is also home to Biltmore Estate (built 1895 by George Vanderbilt, America’s largest private home at 175,000 sq ft, $95 admission).
After touring the mansion and gardens, we browsed galleries in the River Arts District (200+ artist studios). Overnight we stayed at The Windsor Boutique Hotel, a restored 1907 building downtown with suites decorated in eclectic Southern style ($285).
When we took a family trip to Asheville, North Carolina, I quickly realized this mountain town is one of the absolute best hidden gems for a getaway. Nestled in the Blue Ridge Mountains, Asheville has such a vibrant yet cozy energy that made our whole experience feel like a dream.
We spent an afternoon wandering through downtown, where local shops, street performers, and craft breweries created a joyful atmosphere. The mix of historic architecture and cool, artsy murals gave the city such a unique vibe that I couldn’t stop taking photos.
One of my favorite parts was exploring the Biltmore Estate. Walking through the grand halls of America’s largest home and strolling the spectacular gardens felt magical, and even our kids thought it was the coolest part of the trip.
For something a little more adventurous, we headed to the Blue Ridge Parkway. The mountain views were absolutely breathtaking, and we found underrated hiking trails that felt peaceful and exciting all at once.
We also discovered Asheville’s food scene, which was both affordable and exceptional. From quirky cafés serving farm-to-table dishes to unusual donut shops, every meal felt like a brilliant idea. My favorite was sitting outside with live music while enjoying local barbecue—it was such a vibrant family moment.
By the end of the weekend, I knew Asheville was more than just a stop in the mountains—it’s an amazing, family-friendly destination filled with charm, culture, and unforgettable magic.
4. Explore the Rockies in Carbondale, Colorado
We drove about 3 hours 15 minutes west from Denver to Carbondale, nestled at the base of Mount Sopris. Once a coal-mining hub, Carbondale is now an artsy mountain town.
We explored the Carbondale Historical Society’s museums (free, showcasing mining artifacts and pioneer life), wandered Main Street’s galleries, and admired the 19th-century brick storefronts.
When we planned a weekend getaway to Carbondale, Colorado, I had no idea it would turn out to be one of my favorite underrated mountain towns for a family vacation. Nestled in the Roaring Fork Valley near Aspen, Carbondale felt like a hidden gem full of cool surprises and joyful experiences.
We loved walking through the charming downtown, where colorful murals, unique shops, and a vibrant arts scene gave everything an exciting, small-town energy. It instantly felt welcoming and special, like a place we’d want to return to again and again.
One of the absolute best experiences was hiking near Mount Sopris, the spectacular peak that towers over the town. The trails were family-friendly, the air crisp and refreshing, and the views were nothing short of magical. It was a dream backdrop for our family photos.
I thought the most unusual and interesting part of Carbondale was how it blended outdoor adventure with artsy, creative culture. We discovered local galleries, cozy cafés, and even live music that gave our trip a vibrant and memorable twist.
For an affordable and fun family activity, we spent time along the Crystal River. The kids loved splashing in the cool water while we relaxed by the banks, soaking in the peaceful mountain atmosphere—it was an amazing, underrated highlight of our trip.
By the end of our stay, I realized Carbondale is more than just a stop near Aspen—it’s one of the coolest small-town destinations in Colorado, perfect for a family escape filled with adventure, beauty, and a touch of mountain magic.
5. Discover History and Hiking in Charlottesville, Virginia
We drove about 2 hours 30 minutes southwest from Washington, D.C. to Charlottesville. Known as the home of three U.S. presidents, the area is steeped in history. We toured Monticello (Thomas Jefferson’s 5,000-acre plantation, $32 admission), visited the University of Virginia (founded in 1819, UNESCO World Heritage Site), and walked Charlottesville’s historic Downtown Mall (one of the longest pedestrian malls in the U.S., nearly 8 blocks).
Overnight we stayed at the Clifton Inn, a boutique 18th-century estate with 20 rooms and gardens just outside town ($245).
When we visited Charlottesville, Virginia for a family getaway, I was amazed at how this small town combined history, charm, and vibrant energy all in one. Nestled in the foothills of the Blue Ridge Mountains, Charlottesville felt like a hidden gem that offered us the absolute best mix of culture and outdoor fun.
We started our trip exploring the Downtown Mall, one of the coolest pedestrian streets I’ve ever seen. With local shops, lively cafés, and street performers, the atmosphere was so joyful and exciting—it became one of my favorite parts of the trip.
One of the most spectacular experiences was visiting Monticello, Thomas Jefferson’s historic estate. Walking the grounds felt like stepping back in time, and it was both educational and unforgettable for the kids and us. The gardens were especially magical in the afternoon sun.
We also took a scenic drive along Skyline Drive in Shenandoah National Park, which is just a short distance away. The mountain views were absolutely breathtaking, and we found family-friendly hiking trails that made our weekend feel adventurous yet peaceful.
Charlottesville’s food scene was another highlight for me. From affordable farm-to-table restaurants to unique ice cream shops, every meal felt like a brilliant idea. Sitting outdoors under string lights, enjoying local flavors, was one of those spectacular family moments I’ll never forget.
For me, Charlottesville is one of the best underrated towns in Virginia—vibrant, historic, and perfect for a family trip filled with culture, adventure, and plenty of magic.
6. Soak Up the Sun in Myrtle Beach, South Carolina
We drove about 3 hours 30 minutes southeast from Charleston to Myrtle Beach. The city grew in the early 20th century as a seaside resort, with the Myrtle Beach Pavilion and boardwalk opening in 1908.
We strolled along the 1.2-mile Oceanfront Boardwalk, stopped at the SkyWheel (187 feet tall, $16 per ride), and browsed the Franklin G. Burroughs–Simeon B. Chapin Art Museum (free).
Overnight we stayed at the Dayton House Resort, a family-run oceanfront boutique-style hotel with colorful retro charm ($185).
Myrtle Beach, South Carolina is one of the absolute best family vacation spots I’ve ever experienced. Located along the Grand Strand, this vibrant coastal town is filled with exciting attractions, spectacular beaches, and plenty of affordable fun for the whole family.
We spent hours enjoying the wide sandy beach, where the kids built sandcastles and splashed in the waves while I soaked up the sun. The joyful energy of the shoreline made it one of my favorite parts of the trip.
One of the coolest experiences was walking along the Myrtle Beach Boardwalk. With arcades, candy shops, live music, and the SkyWheel offering amazing views of the coast, it felt like a dream destination for families. Every step was exciting and full of magic.
I loved how many underrated attractions we discovered beyond the beach. Ripley’s Aquarium was a brilliant idea for a rainy afternoon, and Broadway at the Beach had unusual shops, cool entertainment, and fun dining options that kept everyone happy.
Our evenings were just as memorable. Watching a spectacular sunset over the ocean, followed by fireworks over the boardwalk, gave us unforgettable moments that I still consider some of the best from our trip.
Myrtle Beach is truly an exceptional small-town getaway with a big personality—romantic for parents, exciting for kids, and absolutely filled with vibrant energy that makes every visit feel magical.
7. Beach It with Ease in Pismo Beach, California
We drove about 3 hours north from Los Angeles to Pismo Beach. Once a mid-20th-century clam-digging capital, the town is still dotted with surf shops and seafood cafés.
We walked along the Pismo Beach Pier (1,200 feet long, rebuilt in 2019), browsed the small downtown, and sampled the city’s signature clam chowder.
Overnight we stayed at Inn at the Pier, a boutique oceanfront hotel with a rooftop bar overlooking the Pacific ($245).
Pismo Beach, California is one of those underrated coastal gems that turned out to be an absolute favorite for our family getaway. Located along California’s Central Coast between San Francisco and Los Angeles, it offers the perfect mix of small-town charm and spectacular ocean views.
We loved strolling along the Pismo Beach Pier, where the kids spotted surfers riding the waves and we caught one of the most magical sunsets I’ve ever seen. It felt like a dream moment, and I couldn’t stop snapping photos.
One of the coolest experiences was visiting the Monarch Butterfly Grove in season. Thousands of butterflies clustered in the eucalyptus trees created such a unique and joyful scene—it was truly unforgettable.
I thought the dunes were the most exciting part of our trip. Renting ATVs and riding across the Oceano Dunes was an unusual adventure that made the weekend feel vibrant and full of energy. It quickly became one of our best family memories.
Downtown Pismo Beach also surprised us with its fun vibe. We explored quirky shops, enjoyed affordable fresh clam chowder at local cafés, and found brilliant little spots for ice cream after dinner.
For me, Pismo Beach is an amazing small-town coastal escape. With its blend of outdoor adventure, unique wildlife, and relaxing beach vibes, it’s the kind of spectacular family destination that feels both cool and magical at the same time.
8. Unplug and Play in Spring Green, Wisconsin
We drove about 3 hours northwest from Milwaukee to Spring Green (population around 1,700). The town is most famous for Frank Lloyd Wright’s Taliesin (established 1911, a 600-acre estate, $35–$125 tours depending on length).
We toured the architect’s studio and home, then strolled the quiet downtown lined with cafés and antique shops.
Spring Green, Wisconsin is one of the most unusual and underrated small towns I’ve visited, and it turned out to be an amazing family getaway. Nestled along the Wisconsin River about an hour from Madison, this hidden gem is filled with culture, nature, and joyful surprises.
We started our trip at Taliesin, Frank Lloyd Wright’s home and studio. Walking through the spectacular architecture and gardens felt like stepping into a dream. It was both educational and inspiring, and easily one of my favorite experiences in Spring Green.
The kids loved our visit to The House on the Rock, a cool and eccentric attraction that felt more like an adventure than a museum. From unusual collections to massive themed rooms, it was one of the absolute best family activities we discovered.
I thought the outdoor experiences were just as special. We hiked at Tower Hill State Park, enjoying peaceful trails and panoramic views of the Wisconsin River Valley. It was affordable, exciting, and a brilliant idea for a relaxing afternoon together.
Downtown Spring Green had a vibrant yet cozy feel, with unique shops, local cafés, and a welcoming small-town charm. We even caught a performance at the American Players Theatre, which made the weekend feel both cultural and magical.
For me, Spring Green is one of the coolest small-town destinations in the Midwest. With its mix of history, nature, and family-friendly attractions, it’s the perfect spot for a spectacular and memorable getaway.
9. Cruise the Chesapeake in Cambridge, Maryland
We drove about 2 hours southeast from Washington, D.C. to Cambridge, one of the oldest colonial towns on the Eastern Shore (founded 1684).
We toured the Harriet Tubman Underground Railroad Visitor Center (opened 2017, free entry, just outside town in the Blackwater National Wildlife Refuge), walked the historic High Street lined with 18th- and 19th-century homes, and explored the Richardson Maritime Museum.
Cambridge, Maryland is one of those underrated small towns that completely won me over for a family getaway. Nestled on the Eastern Shore along the Choptank River, it’s a hidden gem filled with history, waterfront charm, and joyful moments that made our trip unforgettable.
We loved strolling along the scenic waterfront, where the kids watched boats glide by and we all soaked in the peaceful vibe. The sunsets over the river were absolutely spectacular—some of the best I’ve ever seen, and a highlight I captured in my photos.
One of my favorite experiences was visiting the Harriet Tubman Underground Railroad National Historical Park nearby. It felt powerful, educational, and truly unique—an inspiring place that added so much meaning to our family trip.
Downtown Cambridge surprised us with its vibrant energy. We explored cool art galleries, interesting boutiques, and enjoyed affordable seafood at cozy local restaurants. The fresh crab cakes were, without question, the absolute best I’ve ever tasted.
We also found outdoor adventures that made the weekend exciting. From kayaking along Blackwater National Wildlife Refuge to spotting bald eagles in the marshes, every moment felt magical and full of discovery.
For me, Cambridge is one of the coolest small-town destinations on Maryland’s Eastern Shore. With its blend of history, culture, and waterfront beauty, it’s a spectacular family-friendly getaway that feels both peaceful and full of hidden treasures.
10. Make Sweet Memories in Traverse City, Michigan
We drove about 4.5 hours northwest from Detroit (250 miles via I-75 and US-131) to Traverse City (population around 15,000, metro about 150,000). Founded in the 1840s as a lumber town, today it’s known as the “Cherry Capital of the World.”
We explored the Village at Grand Traverse Commons (a 19th-century former asylum, now restored with shops, cafés, and history tours), wandered Front Street’s boutiques, and watched the sunset over Grand Traverse Bay. Overnight we stayed at the Hotel Indigo Traverse City, a boutique downtown hotel with rooftop views of the bay ($215).
The lake shimmered wide and blue, beaches stretching out with sailboats scattered on the horizon. Cherry orchards ringed the town, and farm stands piled baskets high with fruit.
What I Loved Most: Picking cherries straight from the tree, juice staining my hands red.
My highlight? Cherry pie, flaky crust, tart and sweet filling, eaten at a picnic table near the water.
A downside? Summer festivals brought traffic and packed hotels, so planning ahead was key.
Plan your visit:
- Vibe: Lakeside, seasonal
- Highlights: Sleeping Bear Dunes, cherry orchards, Lake Michigan beaches
- Best Time: Summer cherry season
Where to Stay: Great Wolf Lodge has a water park, spa for kids and themed suites with mini log cabins and caves for kids.
11. Teton Village, Wyoming
We drove about 20 minutes northwest from Jackson to Teton Village (population under 500).
Built in the 1960s at the base of the Jackson Hole Mountain Resort, the village blends rustic charm with modern alpine style.
We strolled the cobblestone village, rode the Aerial Tram (4,139 vertical feet in 12 minutes, $45 one way), and learned about the area’s ski history in small lodge displays.
Overnight we stayed at Hotel Terra Jackson Hole, a boutique eco-luxury hotel with modern Western décor and slope-side access ($325).
Traverse City, Michigan has to be one of the absolute best small-town family getaways in the Midwest. Nestled on the shores of Grand Traverse Bay, this vibrant destination felt like a hidden gem that combined lakeside beauty, exciting adventures, and plenty of joyful family moments.
We spent hours at the spectacular beaches, where the kids splashed in the crystal-clear water and built sandcastles while I relaxed under the sun. It was the kind of peaceful yet exciting experience that instantly became one of my favorites.
One of the coolest adventures we had was exploring Sleeping Bear Dunes National Lakeshore, just a short drive away. Climbing the massive dunes and looking out over Lake Michigan felt like a dream—absolutely magical and unforgettable.
Downtown Traverse City had such a unique and vibrant vibe. We wandered through interesting local shops, discovered unusual art galleries, and enjoyed affordable bites at cozy cafés. The cherry pie we tried was hands-down the best I’ve ever had!
Our evenings were just as amazing. We watched a brilliant sunset over the bay, then enjoyed live music while sampling fresh local food at the marina. Every moment felt joyful and spectacular, making the trip even more special.
For me, Traverse City is one of the coolest underrated family vacation spots in Michigan. With its mix of natural beauty, unique charm, and exciting activities, it’s a destination that feels both magical and memorable every single time.
I've written in detail about our adventures in Jackson Hole, Grand Teton and Yellowstone here.
Conclusion
Looking back at all these small-town getaways, I realize the absolute best part of traveling with family is how each place offers its own unique magic.
What I love most is how these destinations—often underrated and affordable—create the kind of experiences that go far beyond just sightseeing. They’re filled with culture, outdoor adventures, unusual discoveries, and simple pleasures like walking through a vibrant downtown or watching a sunset together. Each visit felt like a brilliant idea come to life, and every trip gave us memories I’ll treasure forever.
For me, exploring small towns is the absolute best way to connect as a family. They’re charming, unique, and filled with hidden gems that turn an ordinary weekend into something spectacular. These places prove that you don’t need a big city to have an amazing vacation—you just need a cool little town, an open heart, and the people you love most by your side.
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.
