Theresa Street's 5th Annual Harbor Run

On Sunday, June 7, 2026, enjoy a beautiful run through Westport Rivers Vineyard & Winery in Westport, MA. Grab some friends and enjoy a trail run along gorgeous farms and finishing amongst the vines. After the race, there will be dinner, wine, and music in the vineyard. Race participants will receive a souvenir wine glass as a memento of their experience.

The course is approximately 3 miles along varying trails. The race begins at 1pm with bib pick up starting at 11am, all at Westport Vineyards. Please plan on arriving at least one hour before the race starts to get checked in and settled for an on-time start.

General Race Entry includes parking, race entry, professional race timing, t-shirt, wine glass and wine, dinner and music.

Dinner only includes parking, wine, dinner and music.

For even more information check out our YouTube video and blog.

***New - Join us for the Wine Run tour! Sign up for both the Sakonnet and Westport Wine Runs and SAVE! Select the bundle option.

Please Note: The Wine Run will be happening rain or shine. Because of the logistics of planning for a race of this size, we cannot offer refunds for any reason. If the weather is severe enough to create an unsafe environment for participants, organizers will cancel the event with no refunds issued.

Please join us at our 6th Annual 'Don’t Lose Hope: 5k Run/Walk for Suicide Awareness'!

In 2025, early national data show that the United States continues to lose nearly 50,000 people to suicide each year. Behind every number is a person, a family, and a community forever changed- a reminder of how deeply important connection, support, and accessible mental health care truly are.

Every year, 1 in 5 U.S. adults experiences a mental health condition. Most of us have either lost someone to suicide or know someone who has been touched by it. Now more than ever, we need honest conversations, genuine check‑ins, and a commitment to kindness. Suicide is not a sign of weakness — it’s a sign that someone is carrying more pain than they can manage alone. Let’s be the reason someone feels seen, heard, and supported. Join us in breaking the stigma around mental health by showing your support on Sunday, September 27th.

Run with a p u r p o s e.

Run for a loved one who you've lost to suicide, run for a friend you know is struggling, or run for your own personal mental health battle.

Whatever your reason, you're making a d i f f e r e n c e.

Whether you run, jog, or walk; your presence is what is appreciated most!

Registration will begin at 7:30 am and the official race start time will be 8:30 am. Upon your arrival on race day, please be sure to check in as well as get your honor beads (see below for honor beads description).

PS. If you didn't get to register in time, we will be accepting same-day registrations!

Race Route: