Each town on this list not only promotes walking through their city planning but also offers unique cultural, historical, and recreational opportunities that make each visit memorable.
Whether you’re a lifelong city dweller or looking for a new place to explore, these towns provide the perfect backdrop for both leisurely strolls and energetic explorations.
#27. Hoboken, New Jersey
Hoboken, located just across the Hudson River from Manhattan, offers a dense, walkable urban environment. This small city is characterized by its Victorian brownstones and vibrant street life, with easy access to public transportation, including PATH trains to New York City.
Despite its proximity to the Big Apple, Hoboken has a charm of its own with numerous cafes, boutiques, and waterfront parks. The city is also known for its great schools and family-friendly activities, making it a popular choice for young professionals and families alike.
Why go there: Visit the historical Hoboken Terminal, enjoy the panoramic Manhattan skyline from Pier A Park, and don’t miss out on the famous Carlo’s Bakery for a taste of authentic Italian pastries.
#26. Ithaca, New York
Ithaca is celebrated for its walkability, especially around Cornell University and Ithaca College campuses. The town boasts a lively downtown area, The Commons, which is a pedestrian-only shopping and dining district filled with local art galleries, bookstores, and restaurants.
Surrounded by stunning natural landscapes, including waterfalls and gorges, Ithaca offers an active outdoor lifestyle with numerous hiking and biking trails. The community is tight-knit and supports local agriculture, highlighted by its popular farmer’s market.
Why go there: Explore the scenic gorges, enjoy the vibrant academic community, and take part in the eclectic Ithaca Festival, showcasing local music, art, and cuisine.
#25. Pasadena, California
Pasadena is best known for its walkable downtown district, Old Pasadena, which features a mix of historic buildings and modern amenities. The area is filled with museums, galleries, shops, and restaurants, all within easy walking distance of each other.
The city hosts the annual Rose Parade, attracting visitors from all over to witness the colorful floral floats and festivities. Pasadena is also home to the California Institute of Technology, adding a layer of academic prestige and cultural activities to the city.
Why go there: Attend the Rose Parade, visit the Norton Simon Museum, and enjoy shopping and dining in Old Pasadena.
#24. Alexandria, Virginia
Alexandria’s Old Town is renowned for its well-preserved historic district, offering a charming walkable environment. Cobblestone streets and 18th-century townhouses add to its appeal. The town is filled with boutiques, restaurants, and historic sites, all accessible by foot.
The Potomac River waterfront provides beautiful scenery and a variety of outdoor activities. Alexandria is also home to numerous festivals and events throughout the year, adding to its vibrant community atmosphere.
Why go there: Stroll through the historic Old Town, enjoy waterfront dining, and visit the Torpedo Factory Art Center.
#23. Santa Monica, California
With its iconic pier and expansive beaches, Santa Monica is a favorite for locals and tourists seeking a walkable coastal city. The city’s Third Street Promenade offers a pedestrian-only shopping experience with street performers, trendy shops, and eateries.
Santa Monica is also committed to sustainability, with numerous eco-friendly initiatives and public spaces designed for walking and biking. The city’s laid-back atmosphere is perfect for those looking to enjoy the outdoors year-round.
Why go there: Walk along the Santa Monica Pier, shop at the Third Street Promenade, and relax on the beach.
#22. Savannah, Georgia
Savannah is famous for its large historic district with beautiful public squares, colonial homes, and tree-lined streets. The city’s design encourages walking, allowing visitors and residents to soak in its Southern charm and architecture slowly.
The city hosts a vibrant arts scene and numerous cultural festivals, such as the Savannah Book Festival and the Savannah Music Festival. Its coastal location also offers fresh seafood and unique culinary experiences.
Why go there: Explore the historic squares, enjoy the local art scene, and dine at award-winning restaurants.
#21. Burlington, Vermont
Burlington is known for its lively Church Street Marketplace, a four-block pedestrian zone that is the hub of activity with shops, street vendors, and performers. The city offers a picturesque setting on the shores of Lake Champlain, with extensive trails and parks.
As a college town home to the University of Vermont, Burlington has a young, energetic vibe with a focus on sustainability and local produce, evident in its farmers markets and cooperative groceries.
Why go there: Visit Church Street Marketplace, explore the waterfront on foot, and enjoy local Vermont cheese and craft beer.
#20. Ann Arbor, Michigan
Ann Arbor’s compact downtown area around the University of Michigan is ideal for walking. The town features eclectic shops, galleries, theaters, and restaurants, all clustered near the central campus.
Ann Arbor is also known for its commitment to the arts, hosting events like the Ann Arbor Art Fair, one of the largest in the nation. The town’s parks and riverfront offer additional walking and recreational opportunities.
Why go there: Check out the University of Michigan’s museums, attend the Ann Arbor Art Fair, and walk along the Huron River.
#19. Asheville, North Carolina
Asheville is a mountain town famous for its vibrant arts scene and historic architecture, including the iconic Biltmore Estate. The compact downtown is easy to explore on foot, brimming with art deco buildings, art galleries, and a notable culinary scene.
The surrounding Blue Ridge Mountains provide a stunning backdrop and offer plenty of outdoor adventures like hiking and biking. Asheville’s progressive spirit is seen in its many local breweries and vibrant music venues.
Why go there: Tour the Biltmore Estate, enjoy the local music and art scene, and taste craft beers from local breweries.
#18. Charleston, South Carolina
Charleston’s historic downtown is one of the best-preserved in the U.S., known for its cobblestone streets, horse-drawn carriages, and pre-Civil War architecture. This coastal city is deeply rooted in American history, offering a walking-friendly environment that invites exploration.
The city is also famous for its culinary scene, influenced by its coastal location and Southern heritage. Charleston hosts several cultural events like the Spoleto Festival USA, attracting artists and performers from around the world.
Why go there: Experience the historic Charleston Market, savor Southern cuisine, and attend live performances at the Spoleto Festival.
#17. Key West, Florida
Key West is the southernmost point of the continental U.S., known for its laid-back atmosphere and beautiful historic sites such as Ernest Hemingway’s Home. The town is compact and flat, making it ideal for walking and exploring the colorful homes and tropical gardens.
The local culture features a blend of Caribbean and American influences, evident in its vibrant music scene and culinary specialties. Key West is also famous for its sunset celebrations at Mallory Square.
Why go there: Visit the Ernest Hemingway Home and Museum, enjoy the nightly sunset celebrations, and taste local seafood dishes.
#16. Portland, Maine
Portland’s downtown area is renowned for its walkability, offering a mix of historic charm and modern amenities. The Old Port waterfront features cobblestone streets and quaint brick buildings that house boutiques, galleries, and restaurants.
The city’s cultural offerings include the Portland Museum of Art and a variety of theater productions. Portland’s food scene is also notable, especially for its fresh seafood and innovative dining options.
Why go there: Explore the Old Port, visit the Portland Museum of Art, and indulge in fresh lobster rolls.
#15. Provincetown, Massachusetts
Located at the tip of Cape Cod, Provincetown is a small beach town known for its artists’ community, galleries, and vibrant LGBTQ+ scene. Its narrow, winding streets are lined with boutique shops, art galleries, and seafood eateries, making it perfect for pedestrians.
Provincetown is also a gateway to the Cape Cod National Seashore, offering beautiful beaches and nature trails. The town hosts numerous festivals and events, including the famous Provincetown Carnival.
Why go there: Experience the artistic culture, enjoy the beaches, and participate in the Provincetown Carnival.
#14. Madison, Wisconsin
Madison is nestled between two lakes and features an extensive network of walking paths and bike lanes. The city’s layout promotes walking, especially around the State Capitol and the University of Wisconsin campus. Madison’s State Street is a bustling pedestrian zone that connects the Capitol Square to the university, lined with shops, cafes, and eateries.
The city’s emphasis on parks and open spaces adds to its appeal, with plenty of green areas for relaxation and recreation. Madison also boasts a vibrant cultural scene, with numerous festivals and events year-round.
Why go there: Explore the State Capitol, stroll through the University of Wisconsin’s Arboretum, and enjoy the lively atmosphere on State Street.
#13. Portland, Oregon
Portland is famous for its extensive urban trail system and neighborhood connectivity which encourages walking and cycling. The city’s compact downtown is easy to navigate on foot, featuring an array of independent boutiques, bookstores, and coffee shops.
Known as one of the greenest cities in America, Portland offers a plethora of parks and public spaces, including the expansive Forest Park. The city’s commitment to sustainable living is evident in its many eco-friendly initiatives and community gardens.
Why go there: Visit Powell’s City of Books, explore the laneways for street art, and enjoy a coffee in the Pearl District.
#12. Cambridge, Massachusetts
Cambridge boasts a highly walkable environment, especially around Harvard University and the Massachusetts Institute of Technology (MIT). The city’s rich academic presence fosters a unique cultural and intellectual atmosphere.
Harvard Square is a focal point, bustling with bookstores, cafes, and shops, all easily accessible on foot. Cambridge’s vibrant arts scene and historic architecture also make it an attractive place for walking tours.
Why go there: Tour Harvard and MIT, enjoy the eclectic mix of eateries in Harvard Square, and attend theater performances in Central Square.
#11. Palo Alto, California
Palo Alto, in the heart of Silicon Valley, offers a pedestrian-friendly layout with tree-lined streets and a variety of walking paths. The city’s University Avenue is a vibrant thoroughfare with shops, restaurants, and cafes.
The presence of Stanford University adds to the town’s dynamic atmosphere, with access to university resources, events, and a diverse population. Palo Alto also values green living, with numerous parks and eco-friendly policies.
Why go there: Explore Stanford University, shop and dine on University Avenue, and relax in the many public parks.
#10. Berkeley, California
Berkeley is well-known for its walkable neighborhoods and vibrant street life. The city’s commercial heart, Telegraph Avenue, is famous for its eclectic mix of bookstores, music shops, and cafes.
As home to the University of California, Berkeley, the city thrives with intellectual and cultural activity. The local community supports sustainable and organic food practices, evident in its farmers markets and natural food stores.
Why go there: Visit the UC Berkeley campus, experience the unique shops on Telegraph Avenue, and enjoy local organic produce at the farmers market.
#9. Minneapolis, Minnesota
Minneapolis is renowned for its well-designed walkable neighborhoods and efficient public transportation. The city’s downtown area features the Skyway, an interconnected system of enclosed pedestrian footbridges that protect residents from the harsh winter weather.
Minneapolis also boasts an impressive array of lakes, parks, and bike paths, encouraging an active outdoor lifestyle. The city’s commitment to the arts is visible in its public art installations and thriving theater scene.
Why go there: Walk the Minneapolis Skyway System, enjoy the Chain of Lakes, and attend a performance at the Guthrie Theater.
#8. San Francisco, California
San Francisco is famous for its walkable neighborhoods, such as the bustling Union Square, the historic Mission District, and the picturesque Fisherman’s Wharf. Each neighborhood offers a distinct experience, from upscale shopping and dining to vibrant cultural and historical sites.
The city’s compact size and public transit accessibility make it easy to explore on foot. San Francisco’s hilly terrain provides stunning city views, adding to the walking experience.
Why go there: Ride the historic cable cars, explore Alcatraz Island, and walk across the Golden Gate Bridge.
#7. Boulder, Colorado
Boulder is highly regarded for its pedestrian-friendly design and outdoor lifestyle. The city’s Pearl Street Mall is a central pedestrian zone filled with street performers, local art, and unique shops.
Nestled at the foothills of the Rocky Mountains, Boulder is a haven for outdoor enthusiasts with easy access to hiking and biking trails. The city is also known for its sustainable practices and strong environmental ethos.
Why go there: Stroll along Pearl Street, hike the Flatirons, and participate in the community’s environmental initiatives.
#6. Seattle, Washington
Seattle offers a robust network of pedestrian paths and bike lanes, with areas like Pike Place Market and the waterfront being prime spots for walking. The city’s layout, with its distinct neighborhoods each offering their unique character and attractions, makes it ideal for pedestrians.
Seattle’s cultural scene is vibrant, with a plethora of museums, galleries, and theaters. The city’s proximity to both mountains and water allows for a variety of outdoor activities.
Why go there: Visit the iconic Space Needle, explore Pike Place Market, and take a ferry ride for stunning views of the Puget Sound.
#5. Boston, Massachusetts
Boston’s rich history and compact design make it a premier walking city. The Freedom Trail offers a walk through American Revolutionary history, linking significant historic sites throughout the city.
Boston’s modern side is just as walkable, with neighborhoods like the North End and Back Bay offering charming streets lined with shops and cafes. The city’s emphasis on education and history is palpable, making it a great destination for cultural tourists.
Why go there: Walk the Freedom Trail, visit the museums and historic sites, and enjoy the culinary scene in the North End.
#4. Philadelphia, Pennsylvania
Philadelphia’s historical significance is matched by its walkability. The city is home to Independence Hall and the Liberty Bell, both located within the walkable Independence National Historical Park.
The cityscape blends historic charm with modern vitality, evident in its diverse neighborhoods like Rittenhouse Square and the bustling Reading Terminal Market. Philadelphia’s food scene, including its iconic cheesesteaks, can be best enjoyed by walking through its vibrant streets.
Why go there: Explore historical landmarks, sample local delicacies at Reading Terminal Market, and stroll through the many city squares.
#3. New York, New York
New York City is the epitome of a walking city, with Manhattan offering an extensive array of walkable neighborhoods, each with its own character.
From the bustling streets of Times Square to the serene paths of Central Park, the city caters to walkers of all tastes.
The city’s public transit system supports its walkability, making it easy to get around without a car. New York is also a cultural hub, with endless museums, theaters, and art galleries.
Why go there: Experience the vibrant life of Times Square, explore the museums of the Museum Mile, and enjoy the greenery of Central Park.
#2. Chicago, Illinois
Chicago’s downtown area, including the Magnificent Mile, is a walker’s delight, offering shopping, dining, and impressive architecture.
The city’s extensive lakefront trails provide scenic views of Lake Michigan and numerous parks.
Chicago is also known for its robust arts scene, from world-class museums like the Art Institute of Chicago to thriving live music venues. The city’s diverse neighborhoods, each with their own distinct flavor, are interconnected by an efficient public transit system.
Why go there: Shop on the Magnificent Mile, visit the Art Institute of Chicago, and walk along the Lakefront Trail.
#1. Washington, D.C.
As the nation’s capital, Washington, D.C. is designed for walking, with broad avenues, numerous public squares, and extensive parklands. Iconic landmarks like the Lincoln Memorial, the Washington Monument, and the U.S. Capitol are all connected by the National Mall.
The city is also a cultural treasure trove, with a multitude of free museums from the Smithsonian Institution offering something for everyone. The layout of the city makes it easy to visit multiple attractions on foot.
Why go there: Tour the national monuments and museums, stroll through Georgetown, and attend cultural events at the Kennedy Center.
Methodology
To determine the best walkable towns, I combined firsthand conversations with locals and a deep dive into public reviews.
I spoke with residents and frequent visitors to understand how easy and enjoyable it is to get around on foot—whether for errands, leisure, or daily life.
I also analyzed online reviews from platforms like Google, Reddit, and travel forums to identify consistent praise for walkability, accessibility, and pedestrian-friendly planning.
Sources:
- https://www.citiestosuburbs.com/best-suburbs-for-retirees-moving-out-of-nyc/
- https://www.topretirements.com/reviews/California/Santa%20Monica/
- https://www.pods.com/blog/retiring-in-savannah
- https://www.topretirements.com/reviews/Vermont/Burlington/
- https://www.expatexchange.com/ctryguide/19064/129/United-States/Retire-Ann-Arbor-Retire-in-Ann-Arbor-Guide
- https://www.romanticasheville.com/retirement
Beacon, NY
Good idea. Thank you.
Find a better picture for Portland OR. You used Portland, ME!
Done. Thanks for letting us know.
Wouldn’t even think of visiting San Fran much less walking the feces filled streets.