East Boston's Waterfront Added an Ice Cream Caboose, a Wine Bar, and a Cowboy Bar in One Summer

"I had never dreamed of having an ice cream shop," Troy Retzer said the week he finally opened one anyway.

He wasn't being modest. For five years, Retzer and his business partner Liz Kelley fought city permitting, utility hookups, and a graffiti-covered 1940s train car to turn a dilapidated caboose on the Mary Ellen Welch Greenway into The Blue Caboose, an ice cream and coffee stand at the corner of South Bremen and Marginal streets. When they finally opened on June 3, the neighborhood showed up hard: 350 cones sold on day one, a line down the block for most of opening weekend. The caboose itself has history. A similar car once served as a kitchen for dockworkers unloading ships at the East Boston piers, before trucking replaced that work in the 1950s and left the original sitting empty for decades.

That alone would be a nice local story. What makes it worth paying attention to is what happened around it. In the same five months, this stretch of waterfront near Maverick Square picked up an upscale Italian tavern with skyline views, a wine bar named for a Roman goddess, and city approval for the neighborhood's first cowboy bar. Four openings, four completely different registers of going out, all within a short walk of each other.

A Waterfront That Used to Have One Note

Back in 2019, a Bisnow report on the area described East Boston as a place where "an emphasis on multifamily buildings has kept East Boston largely a bedroom neighborhood that lacks many of the commercial services that draw in modern city dwellers." Big residential towers with names like The Eddy, Portside, and Clippership Wharf had gone up along the water, but the report noted that away from the waterfront, near the Maverick Square T stop, development stayed smaller and slower to arrive.

That framing is years old now, and it shows its age. What's opened along this corridor in 2026 didn't come from one developer with one vision for the neighborhood. It came from a scoop-shop owner who'd been dreaming about a train car since 2021, a hospitality group known for Italian food across four other Greater Boston locations, a café team borrowing flavors from Swampscott and Colombia, and a first-time bar owner who wanted to bring line dancing to the Blue Line. The variety is the story, not any single opening.

Four Different Nights, Four Different Owners

The Blue Caboose runs on simplicity. The menu is Crescent Ridge Dairy Bar ice cream, cold brew and espresso from Recreo Coffee, and matcha or chai from Mem Tea, served through a train window with almost no seating. "We don't have a lot of room, so we can't get crazy," Retzer has said of the approach. Summer hours run 7:45 a.m. to 9 p.m. daily, and Kelley has said she wants the stand open for two seasons a year, summer and fall, with an eye toward Christmas lights and pumpkins once the colder months arrive.

A few blocks away, La Tavernetta opened April 13 at 45 Lewis St., the newest sibling to the Mida restaurant group and the latest project from chef Douglass Williams, who cooked at Radius and at Michelin-starred kitchens in New York and Paris before landing in Boston. Co-owner Seth Gerber has called it "a coastal tavern with an Italian kiss," and the menu backs that up: Calabrian chile wings, striped bass ceviche with aji amarillo and fried yuca, a stromboli filling that changes regularly, and spritzes served in glassware shaped like small handbags. The restaurant sits directly across the water from Mida's original location and is open 11 a.m. to midnight most nights, until 1 a.m. on Fridays and Saturdays.

Pomona Cafe & Wine Bar opened in August, pulling from a wider map than either of the other two. Its name nods to the Roman goddess of fruit trees and to a more formal Pomona cafe already running under different ownership in Swampscott, while the menu itself reaches toward the Mediterranean and across Latin America, including Colombia. It's a daytime café that turns into a wine bar by evening, filling a slot none of the other new openings cover.

Then there's the cowboy bar. On August 27, the Boston Licensing Board approved Joseph Skoczylas's plan to turn the old Eddie C's at 34 Maverick Sq. into what would be East Boston's first cowboy bar, with a closing time of 2 a.m. Skoczylas, who has a decade of experience in restaurant and bar security, has framed it as filling a gap for New England's own community of cowboys, who he says are more numerous and more diverse than people assume. No opening date has been announced yet, so the storefront on Maverick Square is worth watching.

None of this happened in a vacuum. Longtime East Boston spots, including the Italian-American restaurant Pazza and The Tall Ship, a 245-foot vessel turned floating oyster bar moored at Pier One, have anchored the waterfront's dining scene for a while. What changed this year is the range sitting next to them.

Five Years for a Train Car, One Hearing for a Saloon

The contrast in how these places came to be is its own kind of neighborhood texture. The Blue Caboose sat on city-owned land, which meant Retzer and Kelley had to win the space through a public bidding process back in 2021 and then spend years working through permitting, new electrical and plumbing lines, and the removal of roughly 20,000 pounds of steel from the old car before they could serve a single scoop. The cowboy bar, by comparison, needed an afternoon in front of the Boston Licensing Board to get its liquor license approved. Both are legitimate paths to opening a business on the same half-mile of waterfront. They just move at completely different speeds, and residents watching from the sidewalk got to see both timelines play out in the same summer.

The Common Ground Is Piers Park

What ties these openings together geographically is Piers Park, the waterfront green space that sits at the center of this stretch, along with the Harborwalk that connects it to the Greenway and to LoPresti Park a little further down. Piers Park hosted the Boston Lyric Opera's free Street Stage concerts this summer as part of Eastie Weeks, which ran from July 12 through July 29, alongside a ZUMIX concert series, a first-ever bocce tournament on the Greenway, and a kayak program run by NOAH that gave residents free access to the water. The same stretch hosted Taste of Eastie on July 28, the neighborhood's food festival celebrating its 30th anniversary on the waterfront, with longtime vendors like Angela's serving dishes from Puebla, Mexico, alongside Koro Ramen and Sushi, Popsicools, and Mida. A few blocks further, the ICA Watershed has kept its annual exhibition running through the summer, this year with "Lucy Raven: Rounds," giving the corridor an art anchor to go with its food and drink options. LoPresti Park itself adds a 3.4-acre stretch with a ballfield, courts, a splash pad, and its own piece of the Harborwalk, useful for anyone bringing kids along rather than just cocktails.

None of these venues share an owner or a business plan. What they share is a five-minute walking radius, which is what makes the last few months feel less like scattered restaurant news and more like a corridor finding its shape.

What's Open Right Now

As of late September, the Blue Caboose is still serving its fall lineup of coffee and ice cream on the Greenway, with Kelley's stated plan to keep the stand running into the colder months rather than closing for the year. La Tavernetta is open nightly with its late-night Friday and Saturday hours in effect. Pomona is running as a daytime café and evening wine bar. The cowboy bar's storefront at 34 Maverick Sq. is approved but not yet open, so the safest bet for now is to keep an eye on the old Eddie C's sign.

A resident who wanted to see all four in a single evening could start at Piers Park, grab a cone from the caboose, walk a few blocks for dinner with a skyline view at La Tavernetta, and finish by checking whether the lights are finally on at the corner of Chelsea and Maverick.

Four new stops, one short walk, and a waterfront that spent years being described as short on options for exactly this kind of night.

If you're already plotting your own route between the caboose and the cowboy bar, Fenway Group would love to hear which stop wins. Talk to a Fenway neighborhood expert next time you're comparing notes on what's new in Eastie.