Dot Fund Day Opens on Sunday

A new summer tradition is coming to Dorchester! Dot Fun Day, a new open-air market, is set to debut on Sunday, May 31st, in the former Dorchester Tire space — and it sounds like there will be a little something for everyone. Organizers are planning a fun, community-focused setup featuring local food and shopping vendors, craft workshops, kid and pet zones, and, maybe, even a beer garden. The vision? Creating a space where neighbors can gather, hang out, and connect all summer long.

Opening Day Highlights:

• 11am-4pm
• Vendors include Ikigai matcha, diddy burger, pynrs , Lizzie’s bakery (who will there every Sunday)
• VACMass Banh Mì Competition featuring many local banh mi shops and restaurants
• Bounce Houses for kids
• Pet Zone hosted by City Paws

Eat well. Give back. Celebrate Dorchester

Participate before it ends! Looking for a good excuse to grab dinner or a drink in Dorchester? Dine Out DOT is a new fundraising incentive,  giving neighbors the chance to support local restaurants while also helping raise money for the beloved Dorchester Day Parade. Organizers say the fundraiser is all about celebrating the neighborhood and shining a spotlight on the restaurants that help make Dorchester such a vibrant community. Participating restaurants will support parade fundraising efforts over the next few weeks, so every meal out helps give back.  Takes place May 7-31st! Get all the details here!

Enjoy a One-Man-Band Concert at Merry Go Rounds on Friday

Looking for a fun Friday night activity with the kids? Merry Go Rounds in Dorchester is hosting a free, family-friendly concert on Friday, May 29th at 6pm as part of the Greater Ashmont Storefront Sessions. Eric Royer’s One Man Band will be bringing the music — complete with guitar, banjo, harmonica, and plenty of entertainment for all ages. Guests can also enjoy snacks and coupons for in-store shopping while they’re there. Sounds like the perfect excuse to swing by, shop local, and kick off the weekend with some live music!

Get Moving! Free Fitness in the City!

The Boston Parks and Recreation Department and the Boston Public Health Commission (BPHC) are pleased to announce the 2026 Boston Parks Summer Fitness Series sponsored by Blue Cross Blue Shield of Massachusetts. The series offers 22 free weekly classes in City of Boston parks from May 3 to August 29, 2026. The series offers a wide range of classes, including Yoga, Chair Yoga, HIIT,  ZUMBA®, Kick It By Eliza®, Walking Group, Strength and Balance, Line Dancing, Barre Fusion, and Latin Fusion Dance. The program is tailored to residents’ and participants’ interests, including age-friendly classes for families, older adults, and those new to fitness classes. For more information and a link to the full schedule, visit boston.gov/fitness.

Calling all birdwatchers!

Looking for a weekend adventure that mixes hiking, birdwatching, and a little local exploration? The Franklin Park Coalition has you covered with a free Bird Hike through one of Boston’s biggest green spaces on Saturday, May 31st, from 8am-10am. Led by “Nature Man Mike” and the Franklin Park crew, this guided walk will take participants through some of the park’s most scenic spots.  Beginners are more than welcome (and encouraged!) to join. No registration is needed — just show up, bring your curiosity, and if you have them, a pair of binoculars. A few loaners will be available on-site.  Get all the details here.

Free Ferry Weekend

Looking for a free way to get out on Boston Harbor? Free Ferry Weekend returns Saturday, May 30, and Sunday, May 31, offering free round-trip ferry service from Boston to Georges Island.  (Insider’s Tip: Be on the lookout for the Lady in Black.) The annual event, presented by Boston Harbor Now in partnership with the Massachusetts Department of Conservation and Recreation, the National Park Service, and Boston Harbor City Cruises, gives families, residents, and visitors an easy way to experience one of Boston Harbor’s signature destinations without the cost of ferry tickets. Get the details here. 

Pierogis, Polka + Polish Culture and History – Polish Fest 2026

Enjoy a day of culture, fun, food, drink, music + more! On Sunday, May 3st, from 12-6 pm, the Polish American Citizens Club, and the Polish American Heritage and Community Foundation (PAHCF) will be hosting Polish Fest Boston 2026.  This family-friendly annual event allows people from all over the greater Boston area to enjoy the warm hospitality of the Polish community.  This event will feature traditional food, beer, live music, dance, family-friendly activities, and cultural displays.  The event is located just a six-minute walk from Andrew Square Station (Red Line) and the #16, #17, #18, #10, and #5 buses.

Celebrate National Burger Day in Dorchester

As if you really needed an excuse to eat a burger. Well, it’s National Burger Day and we can’t think of a better reason to eat one! Whether you like it with the works or just a little ketchup, today is the perfect day to eat one! We are sharing our picks for the best burgers in the neighborhood! Check them out here.

Broadway Drag Brunch at Blend

Enjoy a Broadway-themed brunch on Sunday, May 31st at Blend. Hosted by @dottieave & @xorosequartzxo come experience live singing, the costume changes, and some delicious brunch in Dorchester! The show is FREE! Just make a reservation on OpenTable.

Azure Day Party at Park City

Get ready to dance because Azure Day Party is bringing those signature outdoor house music vibes to Park City! The party happens on Sunday, May 31st from 3 to 8pm and features music by Luke Alexander. It is a 21+ ticketed event, so get your tickets here! It will be the perfect Sunday Funday!

Take a hike!

Boston Walking City Trails has launched a brand new hiking trail!  The City on the Hills Trail is a 31-mile adventure through some of the best parts of the city. And because we love a good walk (especially if there’s a view and maybe a snack involved), we’re breaking it all down for you, section by section – starting with Trail #5 – Dorchester to Southie – get all the details here! 

SPORTS!

Red Sox vs. Guardians – Friday, May 29th at 7:10pm, Saturday, May 30th at 4:10pm and Sunday, May 31st at 1:40pm.

NBA Playoffs – schedule here

NHL Playoffs – schedule here

Here are 10 places to watch the game in Dot!

Check back as this list may be updated!