• savor + roam
  • Posts
  • What to do in Boston This Weekend (June 20 - 22)

What to do in Boston This Weekend (June 20 - 22)

The official first weekend of summer

Table of Contents

P.S. If you have an event, new attraction, new hotel, or restaurant opening you’d like me to cover, don’t hesitate to reach out.

Like the newsletter? Feel free to buy me a coffee.

food news

How did New England do at the James Beard Awards? Depends on who you ask. The region took home only two awards this year: Sullivan’s Castle Island in South Boston was honored with an America’s Classic Award, while chef Sky Hanuel Kim of Gift Horse in Providence, RI, was named Best Chef in the Northeast. However, many regional favorites made the finalist list, including Cassie Piuma of Somerville’s Sarma (Outstanding Chef), Brookline’s Merai (Best New Bar), and Providence’s Oberlin (Outstanding Restaurant). (savor + roam)

travel news

New travel deals try to tempt Canadians to cross the border. Hotels, campgrounds, golf courses, and even boat marinas near the US/Canadian border have seen a slowdown in bookings. To woo tourists to travel south, many are now offering special discounts just for Canadians. (CNN Travel)

Overtourism closed the Louvre this week. Burnt-out museum workers closed down the world’s most visited museum on Monday, going on strike against the poor working conditions, including “unmanageable crowds and chronic understaffing.” (Afar)

JetBlue cuts more routes thanks to slowed domestic travel. Domestic travel has been slow since January, and to combat the continued economic uncertainty, JetBlue is cutting additional routes. Since last year, the airline has cut more than 50 routes and has pulled out of markets including Baltimore-Washington (BWI), San Antonio (SAT), Burlington (BTV), and Colombia’s Bogotá, Lima, and Quito airports. (The Points Guy)

What is it like to stay in Boston’s Custom House tower? Read about our experience. 

Our Culture, Clarified—Every Week

Every week, 1440 hands knowledge-seekers a guided tour through a single social current. We stitch together history, data, and expert voices so you don’t just witness change—you understand it. One concise, fact-first read turns surface headlines into the deeper “why” that satisfies your curiosity and keeps your worldview expanding.

unique things to do in Boston:
june 20 - june 22

Everything here is happening this weekend only. Scroll down for recurring events every Friday, Saturday, and Sunday in Boston. Like the newsletter? Feel free to buy me a coffee.

all weekend

Boston Pizza Festival, New England’s biggest pizza event, is coming to City Hall Plaza (1 City Hall Square, Boston, MA 02201) from 11 am to 6 pm on Saturday, June 21 and Sunday, June 22. Tickets are $10 and include two slices of pizza with your choice of toppings. Vegan and gluten-free options will be available. Besides over 30 of the best pizzerias in New England, plus pizzerias hailing from Italy, there will be live music, a pizza-tossing station, and an interactive pizza-making demo.

friday
june 20

pride

Gather the girls for Boston Babes Sapphic Girl’s Night Out on Friday, June 20, at Club Cafe (209 Columbus Ave, Boston, MA, 02116). Plans are to head to the dance floor beginning at 8 pm, but people will be hanging out beforehand. This is a free event, with drinks and food available for purchase.

parties + tastings

Looking for a sober way to celebrate a Summer Friday? Cisco Brewers Seaport (85 Northern Ave, Boston, MA 02210) is hosting Best Day Brewing’s Bark & Brew Boston on Friday, June 20, from 1 to 4 pm. Come out for live music, food trucks, and Best Day Brewing’s award-winning craft non-alcoholic beers. This is a free event, with food and drink available for purchase. 100% of Best Day Brewing beer sales will go to benefit MSPCA-Angell.

Celebrate the summer solstice by peering into the future with Venus House at Pretty Moon Summer Solstice pop-up on Friday, June 20, from 4 to 7 pm at Pretty Moon Mercantile (111 Park St, Boston, MA 02132). For $40, you’ll receive a mini astrology reading customized to your needs.

wellness

Flow into the new season with Summer Solstice Yoga with Peter Sacco (Bulldog Flow Boston) and Dray Drinks on Friday, June 20, from 6 to 8 pm at Peter’s Park (230 Shawmut Ave, Boston, MA 02118). Enjoy an hour outdoor yoga session, then head into Dray for a social, NA cocktail hour at Dray Drinks. Tickets are $25.

Or, if you are on the other side of the harbor, attend the Summer Solstice Sunset Flow with The Point Barre and Yoga at Piers Park (95 Marginal St, East Boston, MA 02128) from 7:15 to 8:15 pm. Tickets are $25.

saturday
june 21

festivals, pop-ups, + parties

Boston is honoring Juneteenth with a Juneteenth Celebration at Franklin Park’s Shattuck Picnic Area from 11 am until 7 pm. Enjoy picnics, live music, barbeques, dancing, and more. This is a free event.

Celebrate books, bookstores, history, and more at the rescheduled Harvard Square Bookish Ball on Saturday, June 21, from 11 am to 4 pm in Harvard Square. There will be free literary tours of Harvard Square, promotions from participating stores and businesses, plus free treats, live music, and more. This is a free event.

Spend the afternoon on Boston Harbor for the 11th Annual 90+ Cellars Boston Rose Cruise on Saturday, June 21, from 1:15 - 3:45 (boarding begins at 12:30) on the Spirit of Boston. Tickets are $120 and include three (3) drink tickets for wine, plus buffet-style food throughout the cruise. A cash bar will also be available. Boarding begins at 12:20 pm from Commonwealth Pier at Boston World Trade Center (200 Seaport Blvd, Boston, MA).

Read My Lips, a diverse romance bookstore, is holding a Pop-Up & Free Wine Tasting on Saturday, June 21, from 2 pm to 5 pm at The Urban Grape (303 Columbus Ave, Boston, MA 02116). Read My Lips will have a freshly curated selection of mostly used and some new romance books, including blind dates with books, plus fun swag. 10% of proceeds will go to Network/La Red.

wellness

Start summer with a morning of mindful movement, connection, and restoration at Pause & Thrive: Yoga For Busy Lives on Saturday, June 21, from 10 am - 12:30 pm in Post Office Square (Franklin St, Boston, MA 02110). This free event includes a restorative yoga flow, breathwork, posture lab, journaling, and Reiki. Juicygreens and Smartwater are providing fresh smoothies and energy bites.

sunday
june 22

wellness

Celebrate the year's peak with a one-hour immersive Summer Solstice Breath & Sound Ceremony with Giuliana Gilardo on Sunday, June 22, from 7 to 8 pm at WNDR Boston (500 Washington St, Boston, MA 02111). Tickets are $40. Please bring your own mat.

pride

Grab a pint of Love Conquers Ale and shop LGBT-owned businesses at the Sam Adams Pride Market on Sunday, June 22, from 12 to 5 pm at Sam Adams Boston Brewery (30 Germania St, Boston, MA 02130). This is a free event with food and drink available for purchase.

Shop more queer creators at the Wicked Local Wares Pride Market on Sunady, June 22, from 12 to 5 pm at Time Out Market Boston (401 Park Dr, Boston, MA 02215).

festivals + parties

Help celebrate Prezza’s 25th Anniversary at the 25th Anniversary Block Party on Sunday, June 22, from 12 to 6 pm on Fleet Street in Boston’s North End. Tickets start at $50 and include food and drink stations (depending on ticket), face painting, corn hole, and male.

recurring spring events

As a reminder, the Commuter Rail has $10 weekend passes, which give the ticket holder unlimited travel on Saturday and Sunday. The pass is activated during your first trip on Saturday and remains active until Sunday night.

Like the newsletter? Feel free to buy me a coffee.

tours

Taste your way through Back Bay with a Back Bay Evening Chocolate Tour. For $55, take a guided walking + tasting tour of one of Boston’s most beautiful neighborhoods while learning about Back Bay’s historical and architectural significance. Plus, enjoy tastings at four different locations where you’ll sample hot chocolate, cookies, cupcakes, and cake from Back Bay’s most iconic establishments.

You can find a full rundown of walking tours, bus tours, and trolley tours of Boston in my Beginner’s Guide to Boston.

wellness

Start your weekend with a dose of wellness at The Hidden Art Gallery (25 Myrtle Street) in Beacon Hill, which hosts weekly Explore Meditation with Watercolor classes. Held every Friday from 3 pm - 6 pm, learn the basics of meditation while intuitively creating with watercolor. Classes are $55.

Surround yourself with skyline views during a Saturday Community Yoga session at Rooftop@Revere, on top of Revere Hotel Boston Common (200 Stuart St, Boston, MA 02116), every Saturday from 10 - 11 am. Tickets are $10 and include a post-session smoothie.

If you’ve always wanted to learn how to navigate Boston by bicycle but have been too intimidated to start, join a Weekend In-And-Back Guided Ride with A Better City TMA. On Saturdays and Sundays from 9 am to 1 pm this spring and summer, join a free, three-hour bicycle ride from one of the many bike paths outside the city (meeting location disclosed upon sign up) and traverse their Urban Loop through downtown before returning to the start location.

If you need a weekend pick-me-up, come to The Moxy Boston Downtown (240 Tremont St, Boston 02116) for Rooftop Yoga on Saturdays and Sundays from 9 - 10 am. Led by Julianne Maquire (Saturday) and Claire Metrick (Sunday) from YogaHub, you’ll flow through a dynamic vinyasa yoga experience, expending energizing movement with breath and community. Tickets are $25.

Reconnect with your ability to digest and rest during a Sound Bath Meditation with Ramon of Ib and Flow (247 Walnut St, Brookline, 02445). Sessions ($50) are held every Sunday.

Wind down from the weekend and prepare for the week ahead with a Grounding Meditation session every Sunday from 5 - 6 pm at Blissful Monkey Yoga Studio (663 Centre Street, Boston, 02130) in Jamaica Plain. Led by Licensed Mental Health Counselor Brennan Mallonnee, you will be guided through techniques on how to calm stress responses and practice trauma-informed grounding techniques for anxiety. Tickets are $20. Yoga mats, cushions, and blankets are available, but you can bring your own.

If you’re trying to bring balance into your life this year, start your Sunday brunch with a gentle yoga flow with Brewery Yoga at Lamplighter CX. The class is held every Sunday from 12:30 - 1:30 pm at Lamplighter Brewing Co.’s CX location (110 North First Street, Cambridge, 02141) in their upstairs taproom. Tickets are $25 and include a beer token or a complimentary non-alcoholic drink.

classes + workshops

If you’re new to oysters or want a fun way to spend a sunset this summer, don’t skip Shucking oysters by Boston Harbor with EBO Oysters + EBO Grocery-owner Alex Cervasio. Tickets are $65 and include a hands-on workshop on how to shuck oysters right on a dock in East Boston, fresh oysters, and a shucking knife you’ll get to take home.

Whether you already love screenprinting or are completely new to this printing method, DARK MODE hosts DIY Screenprinting workshops at their storefront in Bow Market (1 Bow Market Way, #24) in Somerville on Friday (7 pm) and Saturday (6 pm and 7 pm) nights. Tickets are $45, including t-shirts.

DARK MODE also hosts Candle Making and Intention Setting Workshops every Thursday at 7 pm in their storefront at Bow Market in Somerville. Tickets are $50.

Spend your Friday learning to make classic Italian cuisine with Self Up Cooking Classes (19 Kingston St) in Downtown Crossing from 6 pm - 9 pm. Every week, they host an Italian Dinner with Tiramisu Finale cooking class and dinner experience, where you can learn how to make a three-course meal, including a luscious tiramisu for dessert. Tickets are $100 and include all ingredients.

tastings + parties

Whether you’re looking to get to know new beers or just a happy hour to kick off the weekend, come out for Hop-Up Series: Local Brewery Tastings at Boston Public Market (100 Hanover St, Boston, MA 02108) on Fridays from 5 - 7 pm. This free tasting features a rotating lineup of breweries, including Dirigible Brewing Co. (June 6), Sam Adams (June 13), and Democracy Brewing (June 27).

Coffee lovers, this one is for you. Every Friday at 10 am, Counter Culture Coffee (374 Somerville Ave) in Somerville opens their Training Center for free coffee tastings. Anyone can learn and connect over perfectly brewed, high-quality, sustainable coffee.

Come to DeLuca’s Market Wine Cellar (11 Charles Street, Boston, MA 02114) in Beacon Hill for a free wine tasting every Friday from 4 - 7 pm. Every week, resident wine expert Donovan handpicks a mix of familiar favorites and bottles from up-and-coming vineyards or hard-to-find vintages to share among participants. No ticket is required.

Every Friday at 6:30 pm, GrandTen Distilling (383 Dorchester Ave) in South Boston holds Friday Night Flights: a chance to get to know their full line-up of spirits (plus special limited-run bottles not available elsewhere) at an intimate tasting. Tickets are $25, and seating is limited (10 max).

On Saturdays, Boston Harbor Distillery (12R Ericsson St, Boston, 02122) leads VIP tours ($50) and barrel-side tastings of their spirits ($20).

Love Child hosts free wine tastings every Friday from 5 pm to 7 pm and Saturday from 12 pm to 3 pm at their South Boston location (364 West Broadway). These tastings are free and require no reservations.

Beginning Friday, May 23, Sam Adams Downtown Boston (60 State St, Boston, MA 02109)will host Decked Out every Friday and Saturday night from 8 - 11 pm into October. Come out for a rooftop hang featuring a different DJ every night. No ticket is necessary; roof access is first come, first served.

Come to The Urban Grape (303 Columbus Ave) in the South End on Saturday for The After Brunch, between 2 pm and 5 pm, for their weekly free wine tasting.

pick-your-own farms

Celebrate strawberry and lavender season with Pick-Your-Own Strawberries and Pick-Your-Own Lavender at Ward’s Berry Farm (614 Main Street, Sharon, MA 02067). Tickets are $15 for a jar of lavender and $7.50 for a pint of strawberries (1/4 peck), wood baskets are $32, 2 quarts are $25, and 4 quarts are $46.

artisan + farmers markets

Shop local artisans every Thursday and Friday at the Downtown Boston Arts Market. Located in Downtown Crossing (8 Summer St, Boston, MA 02110) between Macy’s and Roche Brothers, this outdoor market will recur weekly from 11 am until 5 pm until October 24.

The Boston Open Market returns to Boylston Street, between Arlington and Charles (across from the Boston Public Library), every Saturday through October from 12 to 5 pm.

Alongside the Boston Waterfront, shop over 50 vendors at the Greenway Artisan Market on the Rose Kennedy Greenway. Beginning May 3, the market will be held every Saturday from 11:00 a.m. to 5:00 p.m. and every Saturday and Sunday beginning June 1.

Jamaica Plain holds its weekly Farmers Market every Saturday from 12 pm to 3 pm year-round in the Bank of America parking lot (677 Centre St, Jamaica Plain, 02130).

The Unique Square Farmers Market returns for their 21st season in Somerville’s Union Square Plaza (66-70 Union Square Plaza, Somerville, MA 02143) every Saturday through October 25 (except Sept 20).

One of Boston’s largest open-air markets, SoWa Open Market (500 Harrison Ave, Boston, MA), is held every Sunday from 11 am - 5 pm until October 26. Stop by to shop various regional and local vendors, including food and beverage trucks.

Shop the Seaport Summer Market (88 Seaport Blvd, Boston, MA 02210) every Saturday and Sunday from 11 am to 7 pm. Like the winter market, the summer market is full of unique vendors selling everything from original artwork to pet goods. Food and beverages will also be available for purchase, and a DJ and game area will be available for all ages to enjoy.

Reply

or to participate.