Old Greenwich(United States) Travel 2026: Cheap Flights, Hotels & Top Attractions

In Old Greenwich, the standout boutique hotel is The Inn at Greenwich Village, a charming blend of New England architecture and modern comfort. Located steps from Greenwich Historic District, it offers free breakfast, a private courtyard, and proximity to Greenwich Town Hall and the Connecticut State Museum of Natural History. Its locally curated art and vintage wood interiors reflect authentic town character. Another excellent choice is Greenwich Town House, nestled in a quiet residential area ideal for travelers seeking tranquility and historical ambiance.

The downtown core of Old Greenwich is the prime area for lodging, offering walkability to historic sites, boutiques, and restaurants. Just a 5-minute stroll from Greenwich Town Hall to Old Greenwich Square, this zone features excellent safety, local charm, and access to the scenic Greenwich Riverwalk along the Hudson River. Staying here allows guests to immerse in the town’s cultural rhythm while enjoying convenient access to events and outdoor spaces.

Old Greenwich hosts the annual Greenwich Pumpkin Festival in autumn, featuring hand-carved pumpkins, farmers’ markets, and live folk music. The Old Greenwich Art Gallery regularly showcases local artists with exhibitions on 19th-century rural life. Visitors can also join pottery workshops or explore the Vintage Book Market on weekends—perfect for those seeking authentic, hands-on cultural immersion in a serene New England setting.

Yes, several hotels cater specifically to families. The Greenfield Family Inn offers spacious family suites, a children’s activity room, and safe play areas. They also provide guided tours to nearby attractions like the Connecticut State Museum of Natural History and Greenwich Zoo. Nearby parks such as Hillside Park feature playgrounds and picnic shelters, making it ideal for kids. With its peaceful environment and kid-centric amenities, Old Greenwich is a top destination for family vacations.

Key landmarks include the Old Greenwich Town Hall, with its striking Gothic clock tower; the Greenwich Church Ruins, remnants of 18th-century religious history; and the Memorial Fountain in front of the Old Greenwich Library, surrounded by sculptural gardens. Nature lovers should visit the Hudson River Pathway, where wooded trails and overlooks offer breathtaking views—especially during fall foliage season when the maple-lined paths blaze red and gold.

Old Greenwich excels in locally sourced New England cuisine. Try the cod burger and blueberry muffin at The Old Mill Café, made with ingredients from nearby farms. Another must-try is the slow-cooked beef stew with house-baked bread at Greenwich Farmhouse Bistro, using a family recipe passed down through generations. Don’t miss Hearth & Bean Coffee Co., where artisanal single-origin coffee pairs perfectly with homemade pastries—ideal for a relaxed afternoon break.

Yes, Old Greenwich is highly accessible by car. The Greenwich Transit Hub connects directly to New York City (approx. 45 minutes). Major routes like I-95 Highway provide quick access. Most attractions are within walking distance in the downtown core, and many hotels offer free shuttle services. Additionally, the Greenway Bike Trail system runs throughout the town, enabling eco-friendly exploration of historic districts and riverside views.

Most hotels provide complimentary on-site parking. For example, The Inn at Greenwich Village and Greenfield Family Inn feature ample, secure parking lots. Some older properties may have limited spaces, so it’s wise to confirm availability when HopeGoo. Apartments in the downtown area often include reserved parking spots. Overall, Old Greenwich is very accommodating for drivers, with no steep parking fees or congestion issues.

Absolutely. Old Greenwich exudes romance. Stay at The Willow & Vine Inn, with its intimate courtyard and fireplace suites. Couples can stroll along the Riverwalk at sunset or enjoy an evening at the Old Greenwich Art Gallery with ambient light installations. Dining options like Candlelight Bistro serve candlelit dinners with live jazz. Renting a two-person bicycle to ride the greenway under twilight skies creates a memorable, quiet moment—perfect for anniversaries or honeymoons.

The ideal times to visit are spring (April–June) and autumn (September–November), when temperatures range between 10–20°C. Spring brings blooming flowers and seasonal festivals; autumn dazzles with vibrant foliage along the Hudson River Pathway—a favorite for photographers. Summer is warm but manageable with riverfront escapes; winter features festive lights and holiday markets. Avoiding July heat and December cold ensures a more comfortable, enjoyable trip.