Winthrop is a scenic, coastal community that is a hidden gem nestled away at the beginning of greater Boston’s north shore region. Winthrop celebrates its historic and community assets, while keeping an eye toward building upon them in the future.

Winthrop’s Town Center is home to its main retail shopping and business district along and near Pauline/Jefferson streets and Woodside Avenue. Town Center is anchored by some of its main and celebrated civic and cultural assets. These include signature open spaces like Ingleside Park, French Square, and Metcalf Square, as well as facilities such as Town Hall, and the E.B. Newton Cultural Center and the Arthur T. Cummings Elementary School. Within close proximity and walking distance are some of Winthrop’s well-defined neighborhoods such as Court Park and Cottage Park, as well as the cemetery, the golf course, and Pico and Donovan beaches. Farther afield, and toward shorelines in all directions, one encounters Winthrop’s other neighborhood business districts such as Magee’s Corner, Crest Avenue, Main Street near the Atlantis Marina, and the Crystal Cove area. These districts anchor some of the Town’s other neighborhoods such as the Highlands, Cottage Hill and Point Shirley. Lastly, no matter which direction, one pleasantly stumbles upon one of the Town’s many beaches and coastal ressources such as the Belle Isle Marsh and Inlet.

Looking toward 2030, Winthrop envisions building on the strengths of its neighborhoods’ pleasant streets and nearby shops and parks toward several goals. Pursuing a mixed-use residential strategy that facilitates future development opportunities can allow for additional nearby shops as well as housing options for families, seniors and young professionals. Permissive and proactive initiatives will strengthen neighborhoods through tree protection programs and flood resiliency measures to protect homes’ ground floors.

Winthrop’s committed business community of local restaurants, retail shops and service businesses will flourish and grow thanks to strategic Town decisions and investments. The redevelopment of the former middle school, as well key underutilized commercial and waterfront properties with transformative potential, will deliver an expanded tax base with more jobs, upper-story homes, shopping and customer foot traffic. Investments in streetscape amenities like lighting, seating and shade trees will benefit residents and retail shops alike. Improved streetscapes, parks and beachfronts with new amenities will host outdoor events with food trucks and vendors, and together with a farmer's market will attract visitors and tourists.

Getting to and around Town will include more and frequent options. Residents, commuters and visitors going to or from Town will no longer check schedules for the next Winthrop ferry, or bus headed to the MBTA Blue Line rapid train station. Options for moving around town will be safer and more convenient with traffic calming improvements, bicycle facilities/stations, bus shelters, and a Town shuttle van or trolley circulating between the beaches, neighborhoods, business districts, and the Public Landing.

Winthrop will protect its parks and natural resources by incorporating floodable infrastructure. These include redesigned parks with flood resilient features and plantings, and living shorelines with coastal vegetation to mitigate beach erosion and wave damage. Community resiliency and sustainability efforts will include the installation of solar on municipal buildings for energy reduction.

Winthrop will invest in the development of its children as well as lifelong learners. Building upon the strengths of Winthrop Public Schools’ physical facilities, the Town will strive for competitiveness with teacher retention, and expanding curricular and extracurricular offerings. In addition to successful and beneficial programs such as the Viking Longships, MassSTART and IEP, unique specialty programs leveraging the Belle Isle Marsh Ecology Outdoor Learning Center, or partnerships with organizations or businesses will be pursued for increased opportunities. And lastly, Winthrop’s adults will have awareness of widely promoted educational and career advancement resources such as continued senior education, vocational-technical trades training, and ESL/EFL and financial literacy programs for overall access to opportunities and prosperity.