Downtown Trolley Service Hopes to Run With Worcester Red Sox

Downtown Trolley Service Hopes to Run With Worcester Red Sox

WORCESTER – The Worcester Red Sox inaugural season will kickoff in 2021 — and Worcester residents can literally be along for the ride.

Ride the Woo — a local downtown trolley service start-up — is aiming to launch a fleet of six mini-trolleys to coincide with the opening of Polar Park in Worcester’s Canal District in 2021.

In an interview with [TWIW] on Tuesday, April 23, Aaron Perna, President of Ride the Woo, LLC, said, “We want to launch in time with when Polar Park launches. That’s the timing we are thinking of in trying to build that demand. The construction of the new park gives us time and a platform to promote from.”

The proposed trolley service area, according to Perna — with three trolleys heading in one direction, and three trolleys in the other direction — includes the downtown area around City Hall and the Hanover Theatre, to Polar Park and the Canal District and up Water St., up and down Shrewsbury St., around Washington Square, up Major Taylor Blvd to Grove St. to the new Trolley Yard and then down towards restaurants on Highland St and then back downtown.

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Proposed map of Ride the Woo route

Perna, a Worcester resident and originally of Waltham, told TWIW that it was District 1 City Councilor Sean Rose’s 2018 proposal for a vintage trolley service in Worcester that really sparked his enthusiasm to begin exploring a feasible way to make trolley service a reality in the city.

“Sean Rose has brought this up over the past couple of years and that got me thinking, ‘OK, how can we approach this?’,” Perna said. “If the City doesn’t have the will at this point, and there wasn’t momentum, could we approach it differently?”

Last year, Rose’s proposal for a partnership between the WRTA and a trolley service apparently fell short after it was adopted at the May 1, 2018 Council meeting to be considered by the City Manager.

However, Rose still adamantly supports the notion of trolley service in Worcester.

“A dependable service will be a bonus to the businesses in the downtown and a benefit to those individuals who don’t live close to the downtown and don’t want to have to park in numerous areas while enjoying a night out,” Rose said in an email to TWIW.

Perna raises the same concerns about downtown parking and getting around Worcester as grounds for the trolley service as a necessity in the City.

“One of our biggest gripes was mobility between one area of Worcester to the next — especially before the revitalization of downtown began. Whether you want to eat at one place and go have drinks at another, you have to get in your car or you have to call an Uber just to get around,” Perna said.

“We always thought that having a trolley service would be a good way to connect downtown to these other areas in Worcester,” he added. “For instance, if you wanted to have dinner at deadhorse hill and then grab a beer at Redemption Rock [Brewing Co. on Shrewsbury St.], you can do that by jumping on the trolley and without having to move your car and look for parking at each place you go.”

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The Ride the Woo App

The trolleys Perna is proposing as part of his fleet are mini-trolleys — smaller than transit trolleys in other cities,  with a 13-passenger capacity — and at a relatively inexpensive cost to trolley customers.

According to Perna, having smaller trolleys has its benefits.

“They’re easier to navigate in the tight confines of some downtown Worcester streets. You don’t need a DOT license to drive them. It’s more of a livery service. It creates a lower price point from an operational perspective. You have to think of it more like a shuttle bus — it’s that same level of operation,” Perna said.

Here’s how Ride the Woo will work:

  1. When you Download the App you will receive 2 free tickets to Ride the Woo.   
  2. When you support local businesses, you will be rewarded with more tickets to ride by those businesses as part of loyalty program or other reward program as the business sees fit.
  3. Present the App to the Ride The Woo Trolley driver to redeem your ticket to ride.

“We want this to be a mostly free experience. We don’t want our customers to have to exchange money every time they get on a trolley. The concept is an app by downloading it you get tickets to ride the trolley,” Perna said. “Now the rider is riding quasi-free. They’re paying to ride the trolley by paying for their night out in Worcester.”

Perna envisions the prospect of a number of rewards in unison with local businesses that partner with Ride the Woo, including restaurants and shops.

Ride the Woo is still in its initial phase and Perna and Vice President Ben White are working on generating and showing actual demand for the service before they go to any retailers or business owners to develop partnerships.

Perna calls it “Phase 1” and the company is focused on driving the demand by pushing out their brand on social media to gain a following and build up interest.

Hours of the operation for the trolley service presumably will attract restaurants and entertainment venues. According to Perna, the trolleys will run from 5 PM to 12 AM Thursday and Friday nights, and longer hours on Saturday with the possibility of adding Sunday hours before launching.

“It’s a starting point and subject to change. But we’ve imagined it as an entertainment type of timeline. When are people going out to restaurants and checking out local entertainment,” Perna said.

“Once we have further discussion with businesses and City, if there is demand and people want coverage at different times, then that’s something we will consider,” Perna added.

With the assistance of Rose, Perna and White are working to get the right licenses required by the City and obtaining the correct insurances before they launch.

Councilor Rose would like to see the trolley service as a way to get students from the city’s colleges downtown more frequently and for them to explore what Worcester has to offer outside of campus.

“Right now, there are very few options offered to get our twenty-thousand or so college students into the downtown,” Rose said. “I see substantial economic impact happening as a result of us finding a safe and reliable service to the downtown from different areas of the city.”

Although Perna says Ride the Woo is open to exploring the interconnectivity of the city’s colleges, right now the focus is mastering the concept of the trolley service and being ready to open in time for 2021.

Perna said, “I’m a resident of Worcester that wants the service and wants to see the service happen. To do that, we have to make sure we are prepared well ahead of time, that our partners are lined up and that we have our things in order prior to 2021.”

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    Patrick Sargent is the founder and lead reporter for He was born and raised on Grafton Hill and is a graduate of Holy Name high school and Worcester State University. Over the past two years, he worked as a contributing reporter for the Worcester Sun. Previous to that, over the course of several years, he had stints with GoLocalWorcester, Worcester Magazine, the Leominster Champion and Fitchburg Pride. He is the owner of Sargent Media, LLC and can be contacted at [email protected] or 774-232-1223.