
The Ultimate America 250 Historic Road Trip: Boston to Washington, D.C.
June 1, 2026
A Perfect Day in Manhattan Beach: Beach, Pier, Food and Sunset Photos
June 4, 2026After filming Photowalks in more than 135 locations, I have covered a lot of ground—through big cities, beach towns, historic districts, downtowns and neighborhoods that look great on camera and feel even better on foot.
The best walks have a few things in common. They are easy to navigate, the streets naturally pull you forward, there is always something new to see, and the experience feels made for wandering.
Here are my 2026 “Walkie Awards” for the best walks in America, plus a few bonus destinations that deserve a place on your travel list.
1. San Francisco, California
Best walk for views
San Francisco remains one of the most beautiful cities in the United States, and almost every walk offers a payoff at the top of a hill or around the next corner.
Begin in North Beach, the city’s historic Italian neighborhood, then cross Broadway into Chinatown. From there, climb toward Nob Hill and the Fairmont San Francisco, where the views can stretch toward the bay and Alcatraz.
Continue downhill to Fisherman’s Wharf. Those with energy to spare can keep walking to Crissy Field for a spectacular Golden Gate Bridge finish.
Suggested route: North Beach → Chinatown → Nob Hill → Fisherman’s Wharf → Crissy Field. Time: all day.
2. New York City, New York
Easiest city to navigate on foot
No American city is easier to understand on foot than Manhattan. Once you know that street numbers rise as you head uptown and fall as you head downtown, the grid does most of the work.
The joy of walking New York is that the mood can change completely in just 10 blocks. When you need a break from the urban energy, step into Central Park, where the skyline views from both the East and West sides remind you that you are still in the middle of Manhattan.
Suggested approach: Pick a neighborhood, walk 10 to 20 blocks, then use the New York City Subway when your feet need a rest.
3. Boston, Massachusetts
Best historic walk
Boston’s Freedom Trail is one of the best urban walks anywhere. The 2.5-mile red-brick path connects 16 historic sites and gives visitors a clear route with a constant sense of discovery. Because you’re following the brick path, you can’t get lost.
Along the way, you will pass the final resting places of Paul Revere and John Hancock, then reach the Old North Church, built in 1723 and famous for the lantern signal tied to Paul Revere’s ride. The route continues toward the USS Constitution and Bunker Hill Monument.
Suggested route: Boston Common → Granary Burying Ground → Paul Revere House → Old North Church → USS Constitution → Bunker Hill Monument Time: a good half-day.
4. Chicago, Illinois
Best architectural walk
Chicago is a spectacular walking city in spring, summer and fall. Begin at Millennium Park and photograph Cloud Gate, better known as “The Bean.”
Head north along Michigan Avenue into the Magnificent Mile, a 13-block stretch filled with architecture, storefronts and city energy. Then turn toward the Chicago Riverwalk, where the city opens up and slows down just enough to appreciate the scale of the buildings.
Suggested route: Millennium Park → Michigan Avenue → Magnificent Mile → Chicago Riverwalk Time: half day.
5. Savannah, Georgia
Best city plan
Savannah feels as though it was designed specifically for walkers. The historic center grew around public squares, and 22 of the original 24 remain today.
Start on Bull Street and move through one shaded square after another toward Forsyth Park and its famous fountain. On a second day, visit Bonaventure Cemetery, a beautiful walking destination filled with dramatic trees and memorials.
Suggested route: Bull Street to Johnson Square → Wright Square → Chippewa Square → end in Forsyth Park. Half day.
6. Santa Barbara, California
Best small-city downtown
Santa Barbara proves that a city does not need skyscrapers to offer a great urban walk. The heart of town is State Street, lined with shops, restaurants and side streets worth exploring.
The Spanish-style architecture gives the city its signature look, while the mountains rise in one direction and the ocean waits in the other. The side streets reveal quieter courtyards, older homes and details that often make better travel photos than the main avenue.
Suggested route: State Street → side streets and courtyards → waterfront Time: a good day.
7. Cincinnati, Ohio
Best surprise
Cincinnati is one of the great walking surprises in America.
Begin at Findlay Market, Ohio’s oldest continuously operated public market, then walk through Over-the-Rhine to Washington Park and Cincinnati Music Hall. Continue downtown to Fountain Square and the Tyler Davidson Fountain, then head toward the Ohio River.
Those with extra energy can cross the John A. Roebling Suspension Bridge into Kentucky.
Suggested route: Findlay Market → Washington Park → Cincinnati Music Hall → Fountain Square → Roebling Bridge Time: a day.
8. New Orleans, Louisiana
Best atmosphere
The French Quarter is not a place where the best experience comes from checking off landmarks. It rewards wandering.
Every block seems to reveal wrought-iron balconies, old buildings, courtyards, street musicians, side alleys and cafes. Begin walking without overplanning, follow the sounds and scenes that interest you, and eventually make your way to Jackson Square.
Suggested route: Wander the French Quarter → follow the music → finish at Jackson Square. Then return again at night time.
9. Washington, D.C.
Best monument walk
Start at the U.S. Capitol and head west along the National Mall. Smithsonian museums line both sides, while one landmark after another unfolds ahead.
The walk toward the Lincoln Memorial is roughly two miles, but allow several hours because of the museums, memorials, reflecting pools and photo opportunities along the way. Eleven Smithsonian museums and galleries are located on or near the Mall.
Suggested route: U.S. Capitol → Smithsonian museums → Washington Monument → World War II Memorial → Lincoln Memorial Time: a good day.
10. Venice Beach, California
Best people-watching walk
The Venice Beach Ocean Front Walk is one of Southern California’s great walks because the entire route is the attraction.
The promenade delivers performers, vendors, murals, skaters, beach culture and some of the best people watching anywhere. Major stops include Muscle Beach Venice, the Venice Beach Skatepark, the beach bike path and the Venice Art Walls.
Suggested route: Venice Pier → Ocean Front Walk → Skatepark → Muscle Beach → Venice Art Walls. Time about 2 hours.
Five Great Small-Town Walks
11. Park City, Utah
Best town for trails
Most visitors know Park City for skiing, but the town also has hundreds of miles of trails.
Walk up and down Historic Main Street, then move a few blocks away to the Historic Union Pacific Rail Trail, a wide and mostly flat path. Continue toward McPolin Farm, one of Utah’s most photographed barns.
Suggested route: Historic Main Street → Rail Trail → McPolin Farm Time: a good day.
12. Santa Fe, New Mexico
Best compact history walk
Santa Fe combines history, art, food and architecture in one highly walkable loop.
Begin at the Santa Fe Plaza, then visit the Palace of the Governors, where Native American artists sell their work beneath the portal. Continue to the Georgia O’Keeffe Museum and Loretto Chapel, known for its spiral staircase. Adobe architecture fills nearly every view.
Suggested route: Santa Fe Plaza → Palace of the Governors → Georgia O’Keeffe Museum → Loretto Chapel Time: as long as you want to devote–an hour, two hours, a full day.
13. Avalon, Catalina Island, California
Best car-free island walk
In Avalon, walking is not merely pleasant—it is the natural way to get around.
Walk from one side of the harbor to the other, climb the surrounding hills for elevated views, then return to the waterfront. Catalina Island feels far removed from Los Angeles despite being reached by a roughly one-hour ferry ride from the mainland.
Suggested route: Avalon Harbor → waterfront promenade → hillside viewpoints → return to the harbor
14. Cannon Beach, Oregon
Best little beach-town walk
Cannon Beach has nearly everything visitors want from a small coastal town: galleries, restaurants, candy shops, a long beach and a major natural landmark.
Walk through downtown, then head to the shore and Haystack Rock, the 235-foot sea stack that dominates the view. At low tide, the surrounding tide pools reveal marine life.
Suggested route: Downtown Cannon Beach → galleries and shops → Haystack Rock → beach walk
15. Newport, Rhode Island
Best New England streets and mansions
Newport offers three walks in one: a historic downtown, a working harbor and a mansion-lined coastal path.
Explore the side streets and harbor first, then walk the Newport Cliff Walk, a 3.5-mile public trail beside the Atlantic Ocean and Gilded Age estates. The route offers views of mansions including The Breakers, Marble House and Rough Point.
Suggested route: Historic downtown → harbor → Bellevue Avenue → Cliff Walk
Three Bonus Walks Worth Adding
St. Augustine, Florida
St. Augustine is one of the most photogenic historic towns in America. Walk the old streets, visit the Castillo de San Marcos, built from coquina stone, and see Flagler College, whose centerpiece was once Henry Flagler’s luxurious Ponce de León Hotel.
Victor, Driggs and Tetonia, Idaho
The communities of Teton Valley offer a quieter view of the Tetons than nearby Jackson Hole. Victor, Driggs and Tetonia are surrounded by trails, mountain scenery and the western side of the Teton Range. In Victor, stop at the Victor Emporium for a huckleberry milkshake.
Links to all locations mentioned
San Francisco
New York City
Boston
Chicago
Savannah
- Bull Street
- Forsyth Park
- Bonaventure Cemetery
Santa Barbara
- State Street
- Santa Barbara Waterfront
Cincinnati
- Findlay Market
- Washington Park
- Cincinnati Music Hall
- Fountain Square
- John A. Roebling Suspension Bridge
New Orleans
Washington, D.C.
- U.S. Capitol
- National Mall
- Smithsonian Museums
- Washington Monument
- World War II Memorial
- Lincoln Memorial
Venice Beach
- Venice Beach Ocean Front Walk
- Muscle Beach Venice
- Venice Beach Skatepark
- Venice Art Walls
Park City
- Historic Main Street
- Historic Union Pacific Rail Trail
- McPolin Farm
Santa Fe
- Santa Fe Plaza
- Palace of the Governors
- Georgia O’Keeffe Museum
- Loretto Chapel
Avalon, Catalina Island
Cannon Beach
Newport
- Newport Cliff Walk
- The Breakers
- Marble House
- Rough Point
St. Augustine
Teton Valley, Idaho
Victor EmporiumLinks to all locations mentioned
Teton Valley
Victor
Driggs
Tetonia
San Francisco
New York City
Boston
Chicago
Savannah
Santa Barbara
Cincinnati
- Findlay Market
- Washington Park
- Cincinnati Music Hall
- Fountain Square
- John A. Roebling Suspension Bridge
New Orleans
Washington, D.C.
- U.S. Capitol
- National Mall
- Smithsonian Museums
- Washington Monument
- World War II Memorial
- Lincoln Memorial

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