Self-Guided Walking Tour of Midtown's Historic Landmarks from Penn Station

The route: Penn Station to Grand Central in 10 stops

Penn Station sits beneath Madison Square Garden at 34th Street and Seventh Avenue. It is not beautiful. But it is the starting gun for one of the best walks in the city. Head out the Seventh Avenue exit and you’re already in Midtown.

Here is the route, stop by stop. Every landmark is free to enter.

Stop 1: The James A. Farley Building (Moynihan Train Hall)

Cross Eighth Avenue from Penn Station. The Farley Building takes up the entire block between 31st and 33rd Streets. Built in 1912, it was the original main post office, designed by McKim, Mead & White in the same Beaux-Arts style as the old Penn Station that was demolished in 1963. The inscription across the top (“Neither snow nor rain nor heat nor gloom of night…”) is one of the most quoted lines in New York.

Step inside Moynihan Train Hall to see the skylit atrium that opened in 2021. It gives you a taste of what the original Penn Station felt like.

• Hours: The hall is open daily, roughly 5am to 1am.
• Time needed: 10 to 15 minutes.

Stop 2: Macy’s Herald Square

Walk east on 34th Street to Broadway. The Macy’s Herald Square flagship store has occupied this corner since 1902. The wooden escalators on the lower floors are originals. Even if you are not shopping, the building’s Broadway facade and the old entrance details are worth a look.

• Distance from Farley Building: 3 blocks, about 5 minutes.

Stop 3: The Empire State Building

Continue east on 34th Street to Fifth Avenue. The Empire State Building is 1,454 feet tall, completed in 1931 in just 410 days. You do not need to go up to appreciate it. Stand at the base on the Fifth Avenue side and look straight up. Then step into the Art Deco lobby; it is free to walk through and the ceiling murals are stunning.

• Observatory tickets (if you want to go up): from $44 adults, $38 children (ages 6 to 12). The 86th-floor outdoor deck is the classic experience.
• Lobby hours: Daily, roughly 10am to midnight.
• Time needed: 10 minutes for the lobby; 1 to 2 hours if you go up.

Stop 4: Bryant Park and the New York Public Library

Walk north on Fifth Avenue to 42nd Street. Bryant Park is the backyard of the Stephen A. Schwarzman Building, the main branch of the New York Public Library. In winter, the park hosts a free ice-skating rink and holiday market (late October through early March). Year-round, it is one of the best public spaces in the city.

Then walk around to the Fifth Avenue entrance of the library.

• Distance from Empire State Building: 8 blocks north, about 10 minutes.

What are the must-see highlights and famous film locations inside the main New York Public Library building?

The Stephen A. Schwarzman Building (476 Fifth Avenue) opened in 1911. It is a Beaux-Arts masterpiece, and it is completely free to enter.

Do not miss:

• The Rose Main Reading Room on the third floor. It is 78 feet wide and nearly two football fields long, with 52-foot painted ceilings. This room appeared in Ghostbusters, The Day After Tomorrow, and Sex and the City.
• Astor Hall, the entrance hall with its white marble arches. You have seen it in dozens of films.
• The McGraw Rotunda on the third floor, with murals by Edward Laning.
• Patience and Fortitude, the two marble lions flanking the front steps. Named by Mayor LaGuardia during the Depression.

Hours: Monday, Thursday, Friday, Saturday: 10am to 6pm. Tuesday and Wednesday: 10am to 8pm. Sunday: 1pm to 5pm. Closed major holidays.

Time needed: 30 to 45 minutes for a thorough self-guided visit. Free one-hour tours are offered; check the library’s website for the current schedule.

Stop 5: Times Square (pass through)

From the library, walk west on 42nd Street to Broadway. Times Square is loud, bright, and relentless. You do not need to spend time here, but you should walk through it once. The stretch between 42nd and 47th Streets on Broadway is the core. Look up. The billboards are the point.

• Time needed: 10 minutes to walk through.

Stop 6: Rockefeller Center

Head east on 49th or 50th Street to the Rockefeller Center complex between Fifth and Sixth Avenues. This is 22 acres of Art Deco architecture built in the 1930s.

Key things to see:

• The Channel Gardens on Fifth Avenue between 49th and 50th Streets, leading down to the Lower Plaza.
• The Prometheus statue and the ice-skating rink (open mid-October through April; skating costs around $20 to $40 depending on the session).
• The Rockefeller Center Christmas Tree, on display from late November through early January.
• 30 Rockefeller Plaza (30 Rock): look up at the facade and the Lee Lawrie limestone relief of Wisdom above the entrance.
• Top of the Rock observation deck: $40 adults, $34 children (ages 6 to 12). Open daily 10am to midnight. The views of the Empire State Building and Central Park are better than what you get from the Empire State Building itself.

Time needed: 20 to 40 minutes to walk the complex; longer if you go up to Top of the Rock.

Where can we find a great breakfast spot close to Rockefeller Center before sightseeing?

• Bouchon Bakery (1 Rockefeller Plaza): Thomas Keller’s bakery. Excellent croissants, quiche, and coffee. Opens at 8am on weekdays.
• Le Pain Quotidien (30 Rockefeller Plaza, concourse level): Solid tartines and pastries. Opens at 7am.
• The Diner at 30 Rock (concourse level): Classic diner breakfast, no frills, fast.
• Urbanspace Vanderbilt (230 Park Avenue, closer to Grand Central): A food hall with multiple breakfast options including Roberta’s pizza and Dough doughnuts. Opens at 7am weekdays.

Are there historic churches in Midtown, like St. Patrick’s, that are free to visit inside?

Stop 7: St. Patrick’s Cathedral

Directly across Fifth Avenue from Rockefeller Center at 50th Street. St. Patrick’s Cathedral is the largest decorated Neo-Gothic Catholic cathedral in North America. Construction began in 1858 and it was dedicated in 1879.

Step inside. The nave is 332 feet long. The stained glass windows, many made in Chartres and Nantes, are extraordinary. The baldachin over the high altar is bronze, 57 feet tall.

• Hours: Daily, 6:30am to 8:45pm. Free admission.
• Tip: Visit before 10am or after 5pm to avoid the heaviest crowds.
• Time needed: 15 to 20 minutes.

Other free historic churches in Midtown worth a detour:

• St. Thomas Church (1 West 53rd Street at Fifth Avenue): Episcopal, built 1914, stunning reredos carved from limestone.
• St. Bartholomew’s Church (325 Park Avenue at 51st Street): Byzantine-Romanesque style, 1919. The Romanesque portal was designed by Stanford White.
• Church of St. Mary the Virgin (145 West 46th Street): Known as “Smoky Mary’s.” Anglo-Catholic, ornate interior, surprisingly peaceful given it is steps from Times Square.

All are free to enter during daytime hours.

Stop 8: Saks Fifth Avenue and Fifth Avenue Corridor

Walk south along Fifth Avenue from St. Patrick’s. Saks Fifth Avenue (611 Fifth Avenue) has been here since 1924. During the holiday season (late November through early January), the window displays are elaborate and the light show projected on the building’s facade runs every 10 minutes after dark.

Other notable buildings on this stretch:

• Cartier Mansion (653 Fifth Avenue at 52nd Street): A 1905 townhouse wrapped in red ribbon during the holidays.
• St. Regis Hotel (2 East 55th Street): Beaux-Arts, opened 1904.

Stop 9: The Waldorf Astoria (exterior)

Walk east to Park Avenue and 49th Street. The Waldorf Astoria (301 Park Avenue) is an Art Deco landmark from 1931. It is currently undergoing a major renovation and is closed to the public, but the exterior and the Park Avenue facade are still impressive.

How much time should we allocate to explore Grand Central Terminal?

Stop 10: Grand Central Terminal

Continue south on Park Avenue to 42nd Street. Grand Central Terminal is the final stop on this tour and one of the greatest buildings in the world.

Opened in 1913, designed by the firms of Reed & Stem and Warren & Wetmore. The Main Concourse ceiling is painted with 2,500 stars depicting a Mediterranean winter sky (backwards, by the way; it has been that way since opening day).

What to see:

• The Main Concourse: 275 feet long, 120 feet wide, 125 feet high. Stand in the center and look up.
• The four-faced opal clock atop the information booth. Estimated value: $10 to $20 million.
• The Whispering Gallery outside the Oyster Bar on the lower level. Stand in one corner, face the wall, and whisper. Someone in the opposite corner will hear you perfectly.
• The Campbell (formerly the Campbell Apartment): a cocktail bar in a restored 1920s office with a 25-foot hand-painted ceiling. Enter from 43rd Street and Vanderbilt Avenue.
• Grand Central Market (Lexington Avenue side, lower level): gourmet groceries, good for a snack.

Hours: The terminal is open daily, roughly 5:15am to 2am. Shops and restaurants keep their own hours.

Time needed: 30 to 45 minutes to explore properly.

Tip: Free docent-led tours are offered by the Municipal Art Society on Wednesdays at 12:30pm. Meet at the information booth. No reservation needed.

Practical tips for this walking tour

• Best direction: North from Penn Station, then east to Grand Central. This puts the sun behind you in the morning and keeps the route logical.
• Footwear: Flat, comfortable shoes. You will be on pavement the entire time.
• Restrooms: Available free inside the New York Public Library, Grand Central Terminal, and Bryant Park (year-round).
• Transit home: Grand Central connects to the 4, 5, 6, 7, and S subway lines, plus Metro-North Railroad. You can also walk back to Penn Station in about 15 minutes via 42nd Street.
• Holiday season bonus (late November through early January): Rockefeller Center tree, Saks light show, Bryant Park Winter Village, and holiday window displays at Bergdorf Goodman (754 Fifth Avenue) and Bloomingdale’s (1000 Third Avenue, a bit farther east). The city does the holidays better than anywhere.

Route summary