Westport

Old Hill, Westport Neighborhood

Old Hill presents a tranquil neighborhood with abundant green spaces easily accessible throughout the area. The community features predominantly single detached homes, many boasting four or more bedrooms, offering spacious living arrangements. A mix of architectural styles reflects the neighborhood’s development from earlier decades to more recent times, adding character and variety. Parking availability is generally convenient, supporting ease of travel by car, while several bus lines provide local transit options with stops nearby. Daily needs are met through nearby businesses, including grocery stores and restaurants, creating a well-rounded environment for residents seeking a peaceful setting close to essential services.

Old Hill offers a slower-paced environment and will appeal to those who enjoy spending time outdoors. This neighborhood is very quiet overall, as there isn't a lot of street noise or city clamor. Finally, there are a few parks nearby for residents to unwind in and they are especially well-situated, resulting in them being easy to access from most locations within this part of Westport.

Highlights of Old Hill

Parks, schools, dining, and what makes this neighborhood special

🌳 Winslow Park

Nestled at the edge of Old Hill, Winslow Park is a popular local green space known for its beautiful open fields, shaded walking trails, and fully-fenced dog park, making it a beloved gathering spot for families and pet owners alike.

🏫 Staples High School

Bordering Old Hill on North Avenue, Staples High School is not only Westport’s flagship public high school but also a point of pride for area families, renowned for its award-winning academic, arts, and sports programs.

🍽️ Post Road Eateries

Just minutes from Old Hill, the stretch of Post Road East boasts a variety of beloved local restaurants and coffee shops like The Spotted Horse Tavern and Junior’s Deli, giving residents diverse dining options within easy reach.

🛒 Trader Joe’s Westport

Located on the neighborhood’s southern edge, the Westport Trader Joe’s is a community staple, offering unique groceries and a friendly atmosphere that draws regular shoppers from Old Hill and surrounding areas.

🚴 Saugatuck River Trail

Running near Old Hill, the Saugatuck River Trail offers scenic walking, jogging, and cycling paths along the water, creating a peaceful natural escape that's easily accessible from many neighborhood streets.

Old Hill

This August in Old Hill

Things to do, events, and what's happening this month

August 14, 2026

Storytime on the Green

Jesup Green, Westport Library • 10:00 am–10:30 am

An outdoor storytelling session on Jesup Green is perfect for families from Old Hill looking to enjoy fresh air and community camaraderie just a short walk away.

August 16, 2026

Mayflower II Fuller Shallop Revolutionary Voyage

Westport Historical Society • 11:00 am–3:00 pm

Residents from Old Hill can immerse themselves in local Revolutionary history as the Mayflower II and its crew reenact blockade‑running exploits—a rare and educational community event.

August 19, 2026

Fyütch & Aura V Children's Concert

Levitt Pavilion for the Performing Arts • 6:00 pm lawn opens, 7:00 pm show

A free children’s concert at the riverside Levitt Pavilion gives Old Hill families accessible evening entertainment in a beautiful outdoor setting nearby.

August 2026 (ongoing)

Summer Learning Clubs at Westport Library

Westport Library

Weekly themed STEAM and creative workshops for kids of various ages offer enriching summer learning opportunities conveniently located for Old Hill families.

August 13 – September 10, 2026

The Sin Sisters & Guests – Free Concert Series

Levitt Pavilion for the Performing Arts

Weekly free concerts featuring The Sin Sisters at the Levitt Pavilion give Old Hill residents a scenic, family‑friendly live music option throughout late summer.

From the Neighborhood

Stories, updates, and things to know in Old Hill

Know Your Neighborhood

Local characteristics and demographics for Old Hill

Neighborhood Characteristics

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Demographics

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