How to Spend an Autumn Day in the Village

How to Spend an Autumn Day in the Village

  • Caryl Berenato
  • 10/15/21

As the leaves begin to turn and rain begins to fall, the charm of Greenwich Village is on full display. The cozy coffee shops and dusty bookstores lining the streets seem to come alive as autumn takes hold. Meander along the narrow, tree-lined streets and peek into the neighborhood’s past as you admire the historic buildings. Duck into one of the many eclectic eateries and grab a bite, or peruse some stylish boutiques. Below are some of the best ways to soak up autumn near Manhattan’s Greenwich Village.

Washington Square Park

Washington Square Park is always abuzz with sights and sounds. This vibrant park is a perfect spot for some quintessential New York people-watching, as you’re sure to encounter any number of street performers, artists, musicians, and chess players. Its iconic arch honors George Washington, the man for whom the park is named, and its fountain serves as a popular meeting spot. 

Long before it was a Manhattan icon, Washington Square Park was a tranquil, country respite from the hustle and bustle of the developed downtown neighborhoods. It later became a potter’s field or public burial space, and then a drilling ground for the city’s volunteer militia companies (it was known as the Washington Parade Ground at that time.) Leveled and landscaped, the parade ground conferred a privileged status to the area and helped elevate the value of the surrounding real estate. The parade ground soon became known as Washington Square, esteemed for its patriotic associations and genteel society. Within a few years, the residential neighborhood we know today grew around the parade ground.

Bleecker Street

Bleecker Street was named after Anthony Bleecker, a writer from a prominent New York family who deeded his 20-acre farm to the city. The farm employed hundreds of people and encouraged the growth of local businesses. 

Today, Bleecker Street is a hotspot for nightlife and shopping. You’re sure to find chic boutiques and fine cuisine along this swanky stretch of the Village. 

The Highline


Situated at the far northwest boundary of Greenwich Village, the High Line offers a unique perspective of New York City. This walking trail sits atop a historic, elevated rail line and boasts stunning views of the city, as well as gardens, art, live performances, and food vendors. A serene Manhattan oasis, the High Line is the perfect place for an autumn stroll. 


Early construction of the buildings and residences of Greenwich Village was heavily influenced by Neoclassical architecture. The remnants of this preserved past and quaint historic charm are still alive today. Wandering the streets of the Village and admiring the architecture styles dating back to the late 1700s is a great way to spend a cool, fall afternoon. Here are a few examples of the classic architecture you’ll find in the Village.

Greek Revival

Greek Revival architecture in Greenwich Village typically housed the social elite of the time. The remaining examples of Greek Revival-style houses of the mid-1800s are located along a block of townhouses east of Fifth Avenue called The Row, as well as Colonnade Row, which was once home to aristocrats like the Delanos, Astors, and Vanderbilts. 


Federalist-style architecture typically features semicircular entry porches, louvered shutters, and low-hanging hipped roofs. An example of this style of architecture can be found at Grove Court, a collection of homes boasting original brick façades dating back to the 1820s. 


Popularized in the mid-1800s, Italianate architecture takes after the Picturesque movement, which was a dominant style in Europe a century prior. A group of townhouses at St. Luke’s Place, nestled in the West Village, is a prime example of this style. 

Gothic Revival 

Admire Gothic Revival architecture at Grace Episcopal Church, designed by James Renwick, Jr. Renwick’s later accomplishments include the Smithsonian Institution in Washington, D.C. and St. Patrick’s Cathedral on Fifth Avenue in New York City.

Walking tours

As cheesy as they may seem within an extremely hip neighborhood, a guided walking tour is a great way to spend a fall morning in the city. These guided tours help you explore the Village and offer little-known facts about the artists of this area, including Edgar Allan Poe, Bob Dylan, Jimi Hendrix, and more. 

The Village Alliance offers free self-guided walking tours and provides itineraries and maps about the history and social culture of the area. Tours cover everything from LGBTQ landmarks to important women in history.

Some starting points for a self-guided walking tour include:

  • A glimpse into the Village’s past as you stroll along the cobblestone streets of the Washington Mews. Originally designated as private farmland, this street housed horse stables until the early 1900s, when they were converted into artists' studios. The street was acquired by New York University and is the only remaining privately owned block in Manhattan. It is currently used for language courses and faculty housing.

Credit: Reddit

  • The houses in MacDougal Alley were once stables for the homes on Washington Square North and, similar to the Washington Mews, was eventually turned into studios for artists including Jackson Pollock, Gertrude Vanderbilt Whitney, Japanese sculptor Isamu Noguchi, and sculptor Daniel Chester French.

  • Known for its Bohemian spirit, Greenwich Village is where people explored unconventional lifestyles throughout the 19th century. Famous artists, poets, and musicians have all graced the houses and restaurants in this artistic’ mecca. As the Beat Generation rose to prominence for their counter-cultural lifestyles, icons like Allen Ginsberg, Jackson Pollock, Jack Kerouac, and Frank O’Hara became regulars in the Village’s bars and coffee shops. Follow the footsteps of your favorite Beat icons through a trail of bars, restaurants, and residences, while getting a sense of Village life in the 1950s. Begin your journey at St. Mark's Place, which is a cultural hub abuzz with street vendors, shops, and restaurants. 

Shopping and dining

Enjoy the beautiful fall weather as you dine alfresco at one of the many restaurants offering outdoor seating in the Village. Choose from an eclectic array of cuisine, and every venue from local gems to reservation-only hot spots. 

Dive into a good book or sit back and enjoy people-watching as you dine on the sidewalk of Caffé Reggio, the first café in the country to serve a cappuccino. A beautiful array of artwork adorns the walls, some of which date back to the Italian Renaissance period.

Credit: Olio e Piú

Naples meets New York City at Olio e Piú, a trattoria featuring lush outdoor seating, and fitted with heat lamps to keep you comfortable in the crisp autumn air. The cuisine here is rooted in classic Italian dishes, with a focus on house-made pasta, hand-stretched pizza, and entrées like branzino and Florentine steak.

The farm is truly brought to your table at Loring Place. Enjoy vegetarian small plates, seafood, and locally sourced meat at this holistic Manhattan eatery.

NY Dosa is a vegan stand owned by beloved vendor Thiru “Dosa Man” Kumar. It’s located just beside Washington Square Park, making it the perfect place for people watching while you enjoy savory South Indian crêpes.

Parisian steakhouse meets classic New York City tavern at Minetta Tavern. This restaurant was frequented by Ernest Hemingway, Ezra Pound, Eugene O'Neill, E. E. Cummings, Dylan Thomas, Joe Gould, and other literary icons. 

Wicked Jane offers fine dining with dishes like sea urchin, duck breast, and foie gras cannoli.

Once you’ve dined your way through the Village, browse the diverse array of shops offering everything from vintage clothing, books, records, boutique brands, and more.

Farmers’ markets

Fall is a perfect time to peruse outdoor farmers’ markets for fresh seasonal fare. The Abingdon Square Greenmarket offers heirloom vegetables, fruit, fresh-caught fish, and artisanal goat and cow's milk cheeses. The Astor Place Greenmarket features a selection of locally grown vegetables and orchard fruits, baked goods, cider, jams, maple syrup, and honey from regional farmers.

Annual Halloween Parade

The NYC Halloween Parade is a cherished spectacle. Each year, approximately 50,000 revelers parade up Sixth Avenue donning handmade costumes. Join the parade with your own costume creation, or admire the madness from the sidelines. 


Enjoy the vibrant colors and changing leaves while relaxing in one of the Village’s green spaces. Some local favorites include:


Moving to Greenwich Village?

Whether you’re looking for a scenic walk, eclectic shops, or dining and relaxation, Greenwich Village’s walkability offers plenty of opportunities to enjoy the crisp autumn air.

If you’re interested in investing in the vintage New York City charm of Greenwich Village, contact local expert Caryl Berenato and her trusted team of realtors.


*Header image credit: Whitney Museum


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