- Recommended
Stamford History Center
Stamford's leading local history museum covers the city's colonial, industrial, and social past through changing exhibitions and archives.
Take a bus from Winthrop, MA to Stamford, CT and enjoy the approximately 160 miles (258 km) long journey. Find schedules and pricing options for a convenient and affordable trip.
The earliest bus runs at 05:00, the last at 22:40.
Distance 160 miles (258 km) |
First bus 5:00 AM |
Last bus 10:40 PM |
Discover the best of Stamford, CT — top attractions, local food, transport tips, budget advice, and currency essentials. Plan your perfect Stamford, CT trip today.
Stamford's leading local history museum covers the city's colonial, industrial, and social past through changing exhibitions and archives.
A contemporary nonprofit gallery featuring regional and international artists, valued for ambitious exhibitions and creative programming.
This nature center includes educational exhibits on local wildlife and habitats, making it a family-friendly museum-style stop.
Stamford's signature waterfront park offers beaches, walking paths, a carousel, and broad Long Island Sound views for an easy escape.
A large urban park with gardens, trails, sports fields, and seasonal events, popular with both locals and families.
This downtown public square hosts concerts, markets, and winter skating, making it a lively gathering place year-round.
A thick Greek-style pizza with an oily, crisp crust and rectangular slices. A Connecticut classic common in local pizzerias and taverns.
A split hot dog topped with mustard, relish, onions and bacon or cheese. Popular in southern Connecticut for a quick local bite.
A lobster roll served warm with melted butter on a toasted bun. A signature Connecticut seafood dish enjoyed along the coast.
Established Italian restaurant popular for handmade pasta, seafood and elegant dining suited to special occasions.
Classic upscale steakhouse known for dry-aged beef, seafood and polished service in a refined downtown setting.
Lively modern Mexican restaurant and tequila bar known for tacos, guacamole and a stylish, energetic atmosphere.
More expensive than many U.S. cities. Hotels, dining, and parking are high; local transit is limited, so visitors often rely on Metro-North, rideshares, or taxis.
Tip 18-20% at restaurants, more for excellent service. Round up or tip 10-15% for taxis. Cafes often have tip jars or screen prompts for $1-2 or 10-15%.
Find answers to the most common questions about traveling from Winthrop, MA to Stamford, CT by bus. From journey times and ticket prices to direct connections, first and last departures, and even whether the route is scenic, our FAQs cover everything you need to plan your trip. Whether you’re looking for the fastest bus, the cheapest option, or tips for making the most of your visit at Stamford, CT, this guide helps you travel smarter and with confidence.

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