Walk to the end of Medford Street on a cold November morning. You'll find a softball field with a seawall on one side, Little Mystic Plaza's shade trees on the other, and the channel water past the outfield. Barry Playground is affectionately known as "The Oily." On October 30, the Charlestown Patriot-Bridge reported that it had won a $1 million grant.
Barry is the last project in line along the Little Mystic Channel. Some of the waterfront around it has already been rebuilt and is open to walk on. One stretch of path is about to go under construction. A much bigger park on Alford Street is halfway through a rebuild. The grant goes to the project scheduled to start last. That order matters for anyone who uses this part of Charlestown, and it's easiest to follow from the pieces that are already done.
What you can walk today
Two of the projects are already finished.
The first is the Barry Playground Connector, which Massport completed in 2024. It's an accessible walking and biking link between Barry Playground and Chelsea Street. According to the Mystic River Watershed Association, it filled a missing link in the Boston Harborwalk and lets people move easily between the Little Mystic Channel and the Navy Yard.
At the Navy Yard end of that walk, the National Park Service has just started its own long project. Rehabilitation of Building 107 began this fall. Built in 1904, it's a national historic landmark that once housed the Navy Yard's tradespeople. The roughly $50.2 million renovation will turn it into the headquarters for Boston National Historical Park, the Patriot-Bridge reported.
The second finished piece is Little Mystic Plaza, right next to Barry Field and CharlesNewtown. The Mystic River Watershed Association led the design and construction and finished in 2025. It turned 9,000 square feet of bare asphalt into an open space with 52 shade trees, an accessible lawn, plenty of seating, and a public mural. The association marked the opening that June. It also received a small grant for multilingual signs. Each tree gets an identification tag, and eight panels explain how each species helps the local habitat and the community.
A little farther along are the Charlestown Sprouts Community Garden and the Charlestown High School athletic fields, which were resurfaced in 2024.
The ballfields, playgrounds, and the last stretch of path are still to come.
The gap on Terminal Street is next
The Harborwalk still has one break around the channel. The Little Mystic Harborwalk Extension will fill it with a 1,000-foot segment running from the current end of the path at the Little Mystic Boat Ramp. Plans call for a 10-foot-wide accessible path, shaded seating, native plantings, and exercise equipment.
This project now has contractors. The Boston Planning and Development Agency's board met on October 15. Its published agenda asked to authorize a $5,146,127.71 construction contract with Unified Contracting Inc. It also asked to authorize a construction-management contract with HDR Engineering, Inc. capped at $418,862 with contingency. A post-meeting roundup from Sundays reported that the board authorized both contracts and that the project is expected to take 18 months.
The street work around it is part of the plan too. The intersection of Chelsea Street and Terminal Street will get a traffic signal with its own pedestrian phase. A new crosswalk there will connect the Harborwalk Extension to the existing Chelsea Street sidewalks.
The Watershed Association's own schedule puts the extension's construction in 2026 and 2027. Two more projects nearby, an Urban Meadow between Charlestown Sprouts and the boat ramp and an upgrade of the boat ramp itself, are still in early design. The boat ramp is one of only two public boat ramps in the city.
Ryan Playground is the one to watch
Barry's place in line makes more sense once you look upriver at Ryan Playground on Alford Street.
Ryan is under construction. The city is spending $16 million on its second phase, with Weston & Sampson as the design consultant and Fleming Bros. Inc. as the contractor. The city's September 2026 construction update shows how far the ballfield work has come:
- All backstops and scoreboards are in.
- The Little League practice field has turf.
- The softball diamond is being prepared for its infield.
- The Babe Ruth baseball backstop, fence posts, and base-path infield dividers are installed.
- Irrigation and water lines are done, and electrical cabinets now line Alford Street.
The October work list covered planting trees before the first frost and starting concrete footings for the playground equipment. The city expects the park to reopen in Fall 2027. The finished park will include ballfields, a playground, a splash pad, and lighting.
The two parks are linked. At a November 2025 community meeting, Barry's softball field was described as getting little use apart from overflow while Ryan was under construction. Ryan is expected back in fall 2027, and Barry's construction is scheduled to begin in 2027.
Here is the full order as the published schedules have it:
- Barry Playground Connector, completed 2024
- Little Mystic Plaza, completed 2025
- Little Mystic Harborwalk Extension, contracts authorized October 2026, about 18 months of work
- Ryan Playground, reopening expected Fall 2027
- Barry Playground, construction scheduled to begin 2027
What the grant pays for at the Oily
The grant comes from the Land and Water Conservation Fund. The state Executive Office of Energy and Environmental Affairs runs that program for the National Park Service. Barry was one of 14 projects in a statewide round worth nearly $10 million.
The redesign keeps the softball field and upgrades it, and adds the following:
- an accessible 1,500-foot walking loop around the field, which raises the existing Harborwalk
- spray play and misting structures
- fitness equipment for all ages
- terraced seating and a small plaza with game tables
- more shade trees and canopy
- a small food forest
"This redesign will create a more welcoming space for children and families to play, connect, and cool off in the summer," Boston Parks Commissioner Diane Fernandez Bibeau said in the Patriot-Bridge report. In the same article, State Rep. Dan Ryan tied the grant to "the extensive work being done at Barry and the Little Mystic Channel." Charlestown Neighborhood Council Chair Tom Cunha called the plans "a perfect complement to the renovations being done at nearby Ryan Playground."
The design is still moving through approvals. Weston & Sampson, which is also designing Ryan, presented the plans at a third community meeting on August 5. The meeting minutes and a follow-up agenda show the project going before the Conservation Commission, a Chapter 91 waterways filing, review by the Boston Water and Sewer Commission, and review by the state's coastal zone office and the U.S. Army Corps of Engineers.
The neighborhood's requests made it into the August meeting minutes. One was for hopscotch, four square, and fish and animal outlines that kids could color in with chalk. Another was for a marker for the "Mouth of the Mystic River." The Parks Department said it is working on that marker with Boston Harbor Now as a sign with substantial historical content. The minutes also mention a local hero's marker that used to stand in the park and is now gone, most likely honoring William J. Barry. The city's answer was that the park will have three historic signs. The existing trees along the edge won't stay. The designers said those trees are damaging the seawall and mostly shade the wall and the water rather than the park.
This winter and next
For now, the Little Mystic edge is a walking route. You can go from Chelsea Street over the Massport connector, past Barry Field, through the plaza's 52 trees, and on to the boat ramp. The Terminal Street segment past the ramp is next to be built. Ryan's ballfields and splash pad are due back in fall 2027. Construction of Barry's spray play, game tables, and 1,500-foot loop is scheduled to begin in 2027.
If you're wondering how this rebuild of the Little Mystic waterfront could affect a home you own or are thinking about near Medford Street, Terminal Street, or Alford Street, Tracy Shea and the team follow these projects closely and are glad to walk the area with you. Schedule a Consultation, and we'll start at the Oily.
