Summer of Dreams: Things to Do in Boston THIS Summer!

Things to Do in Boston This Summer!

Well friends, we made it. Summer 2021, aka summer of dreams! Restrictions are lifted, masks are off, so let the good times roll. Boston is ready for a summer of food, fun, and frolicking. We’ve got just the list to get you started. We know summer still technically doesn’t start for another couple of weeks, but we can’t wait one moment longer. So… ready, set, SUMMER OF DREAMS!

24. Shop Local at SoWa Open Market

Photo Credit: SoWa

The SoWa Open Market returns this summer to Boston’s South End, giving local artists and makers a place to display and sell their creations, while getting some face time with their customers. This celebration of local makers is a wonderful way to support the community and spend a Sunday afternoon outside this summer in Boston. The market is open every Sunday from 11am to 3pm.

23. Fun in the Sun at Castle Island

Photo Credit: @willscitylife via Instagram

Castle Island is always a great local day trip for some summer fun in Boston. Whether you live down the street in Southie, or have to commute, it’s full of summer vibes. From the harbor walk to the beach to the historic sites there you can easily fill an afternoon. And don’t forget about the grub! Sullivan’s is legendary for their fried seafood and snacks so refuel there before enjoying the rest of your fun in the sun.

22. Take a Neighborhood Food Tour with Bites of Boston

Hands down one of the best ways to experience a neighborhood is through its food. And food is best enjoyed with company. So grab your friends, family, significant other, or random person from the street, ok maybe too soon for that, and join us for a walking neighborhood food tour. You’ll explore the landscape and history of one of Boston’s most unique neighborhoods, enjoying the summer weather, while getting to learn about it from the lens of its amazing food. All of our tours include both sweet and savory tastings so come ready to eat, experience, and explore!

21. Take a Beach Yoga Class with Open Doors Dorchester

Photo Credit: Open Doors Yoga Dorchester

Now that we’re free to frolic outside of our houses, if you’re wanting to do everything but just can’t fit it all in, then hit two of your summer to-dos with this activity — beach yoga! You’ll get your workout and your beach time all in one with the added bonus of being zenned out. Not bad right? Open Doors Yoga in Dorchester is hosting three yoga classes per week on Malibu Beach. No not that Malibu. But, it’s still nice! Choose either a sunset class on Monday or Wednesday night or a morning power flow to start your weekend on Saturday morning. It’s a great way to celebrate summer in Boston.

20. Eat Seafood at The Barking Crab

Photo Credit: The Barking Crab

At the top of our list of celebrating summer in Boston is eating alllll the fried seafood we can get our hands on. While we might have to keep some Tums handy, we’re committed! We love The Barking Crab for both its food and its atmosphere, which is why it has become a favorite eating and meeting place for Bostonians since it opened in 1994. Located on Boston’s historic Fort Point Channel at the gateway to the Seaport District, The Barking Crab will satisfy all of your summer seafood needs from steamed to fried, all while you enjoy some time outdoors by the water.

19. Enjoy Live Music Outside at The Boston Harbor Hotel

Photo Credit: @loulou4743 via Instagram

LIVE. MUSIC. IS. BACK. And we are sooo excited about it! There is nothing better than sipping some wine on a summer night and listening to live music be performed. The Summer in the City series hosted by the Boston Harbor Hotel at Rowes Wharf is back in action with a lineup of free entertainment from music to movies and more. Events are held every Tuesday through Friday from 6:00-10:00pm where performers of all kinds will take center stage on the floating barge (it’s anchored, don’t worry) to put on a show that will help you enjoy a summer night in Boston.

18. Walk Through the Arnold Arboretum at Harvard University

Photo Credit: Arnold Arboretum

For a scenic walk right in the city head to the Arnold Arboretum of Harvard University. It is a museum of trees teaching the world about plants and providing a beautiful atmosphere to spend a summer afternoon. The community is made up of researchers, volunteers, professors, educators, artists, gardeners, caretakers, and everyone in between. The Arboretum is a 281-acre preserve in the heart of Boston that stewards one of the world’s most comprehensive and best documented collections of temperate woody plants, with particular focus on the floras of eastern North America and eastern Asia. A beautiful and educational place for a summer stroll.

17. Explore Boston’s Food Truck Scene

Photo Credit: Just Wingin’ It

Boston’s food truck scene is once again bumping! After being hit hard by pandemic regulations the food trucks are back out on the prowl on the streets of Boston. Boston prides itself on some of the most creative and diverse food trucks. Check out the full schedule to see who is parked where and when. You’ll find everything from Bibimbap to garlic Parmesan wings to a fluffernutter sopapilla pocket and more. Go ahead, get on it!

16. Eat on Oleana’s Garden Patio

Photo Credit: Oleana

Oleana has arguably one of the best patios in Boston, well technically it’s in Cambridge, but I still say best in all of Boston. This magical garden hideaway is tucked behind the restaurant from which you’ll find the most stunning and delicious Eastern Mediterranean dishes coming from a teeny tiny female-run kitchen. This place is the full package from flavor to ambiance to service and it’s a nice little local getaway for a summer meal. Make sure to reserve ahead of time because now that they are back to full capacity people will be lining up to get a spot!

15. Visit Boston Public Market

Photo Credit: Boston Public Market

The Boston Public Market is another place that celebrates local chefs and makers and is open all week long for you to enjoy! It’s a great way to find reprieve and refuel from the summer heat as it’s inside. Pop in on your summer city adventure and grab a snack (or several) to eat there and then of course some provisions to go for later. Everything sold at the Market is produced or originates in New England, as the seasons allow.

14. Explore the Charles River with Paddle Boston

Photo Credit: Paddle Boston

If you are more of the get up and go type and you like to enjoy summer being active then start shedding that COVID 10, 20… we’ll stop counting, while kayaking or canoeing on the Charles River. This is a great way to get some sun, get some exercise, and spend time with friends. Paddle Boston offers boat rentals as well as river tours so hop aboard and get to paddling!

13. Dine Out on a Rooftop

Photo Credit: Six West

If lounging and sipping are more of your groove then look no further because we’re experts on those two things. Head to one of Boston’s amazing rooftop decks for some sipping and snacking with a view and do summer 2021 right. We’ve got a whole summer to make up for so we’re not messing around. Some of our favorite spots include: The Lexington, Six West, and Pier 6, but there are more!

*Fun fact: Pier 6 offers a complementary water shuttle to its sister restaurant Reel House in East Boston so you can have drinks and apps at another place and entrees and dessert at another, or however you want to work it!

12. Spend Time on the Water with Boston Lux Cruises

Photo Credit: Boston Lux Cruises

Did someone say luxury cruise? No. Well, we’re going with it and you’ll want to too once you see what this is all about! The new Boston Lux Cruises is ready to take you out in style making you feel like you chartered a luxury yacht. Well maybe that is taking it a little too far, but they will serve endless drinks and snacks while cruising you around Boston Harbor. Get fancy as you sit back and relax and let summer 2021 be the summer of dreams. We knew you’d get on board *wink*.

11. Dine, Drink & Shop at Bow Market

Photo Credit: Bow Market

Bow market is another hidden gem where you could easy spend a summer day frolicking, and by frolicking we mean eating, drinking, and shopping, duh. From your first cup of coffee to your last round, and every meal and errand in between, Bow Market offers award-winning choices, right in the neighborhood and a lovely seating area to rest in between. Bow Market has quickly become a hub for the area’s most creative and collaborative. From chefs and comics to DJs and designers, it’s a must-stop-spot for the best in small business and local entertainment.

10. Drink BEER

Photo Credit: Dorchester Brewing Co.

Boston is best known for its brews and for those who like to drink ’em. Celebrate summer 2021 with some pints of ice cold beer on a beer garden or patio. So many of Boston’s favorite local breweries have spacious beer gardens or patios for you to sit back and relax this summer. Some of our favorites include: Lamplighter Brewing Co., Trillium Brewing Co., and Dorchester Brewing Company, but there are so many more. Cheers friends!

9. Weekly Wine Dinner at Forage

Photo Credit: Forage

While we’re on the topic of booze…if wine is more your jam, then join Forage in Cambridge for their weekly wine dinner every Tuesday night. Forage is a neighborhood bistro right outside of Harvard Square. Through partnerships with local farmers, fishermen, and foragers they offer a local, seasonal ingredient-driven menu served in a casual setting.

8. Cheap Date Night Thursday at Bodega Canal

Photo Credit: Bodega Canal

If you’re on that dating grind this summer then we have the perfect spot for you to eat on the cheap but feel like you’re splurging. Bodega Canal has brought back their Cheap Date Night offering on Thursday nights where you and your date can enjoy a 3 course meal for $30 total! This is a steal and leaves room in the budget for the most important date night detail…the booze!

7. Brunch Test Kitchen at Lincoln Tavern

Photo Credit: Lincoln Tavern

Looking to elevate your brunch game in 2021? Lincoln Tavern has you covered. Brunch Test Kitchen is a rotating brunch menu that they offer in addition to their lunch menu every Friday from 10am-3pm. Each week they prepare a new and creative menu for those guests who may be sick of the same old lunch or are looking for a creative take on brunch! Brunch Test Kitchen favorites (like their Fruity Pebble Pancakes) eventually make their way to the regular brunch menu available on Saturday and Sunday from 10am-3pm.

6. Veuve & Groove Brunch at Rail Stop

Photo Credit: Rail Stop

Bubbles, brunch, and beats, YES PLEASE! Saturday is for brunch and Rail Stop has created their own brunch tradition featuring, most importantly, Vueuve Clicquot by the bottle, your favorite over-the-top brunch dishes, specialty brunch cocktails, and groovy beats in the background. Enjoy brunch classics like Lobster Benedict, Ricotta Pancakes, Prime Rib Hash, and Bloody Marys, but also Veuve Clicquot, indulgent chilled seafood towers with dry ice, mimosa mixer flights, and more – while grooving to a bumping playlist! Every Saturday from 11:30am-3pm. Call to book.

5. Set Sail with Classic Sail Boston

Photo Credit: Classic Sail Boston

Classic Sail Boston has been showing people the best of Boston Harbor since 2014. Their goal is to make each of their charters a memorable and unique experience for guests. Whether theming around a special occasion or just enjoying an afternoon on the water,  they will customize and design the perfect environment according to your specifications. Sit back, relax, and sail in style!

4. Sip Cocktails at Citrus & Salt

Photo Credit: Citrus & Salt

There is nothing that says celebration more than a cocktail from Citrus & Salt. We’ve got tequila on our minds as a matter of fact and so do they. Their Tequila on My Mind cocktail can be made shareable so pass out the straws and get to sippin’. These cocktail are not only visually appealing but delicious and creative. What better way to have a summer of dreams than with a gorgeous cocktail to cheers the kick off?

3. Stroll the Rose Kennedy Greenway and Ride the Carousel

Photo Credit: Rose Kennedy Greenway

There’s always something going on at The Greenway. Whether you want to taste the latest from local restaurants, relax in an urban oasis, or ride on a contemporary carousel, you’ll find fun around every corner. It’s a great place to head without a plan and just let things unfold from eating to exploring to unwinding, this is a great place to go in the summer in Boston.

2. Eat Ice Cream from The Scoop N Scootery (or get it delivered)

Photo Credit: Scoop N Scootery

If these guys know one thing in and out it’s ICE CREAM; and when it comes to ice cream we’re not messing around. The Scoop N Scootery began out of a food truck as an ice cream delivery concept. Over the past six years the team has worked to perfect the perfect sundae, the speediest delivery methods, and opened three brick and mortar locations. In 2019 Grubhub even ranked them as #1 dessert delivery shop in America. Like we said, we don’t mess around when it comes to who is scooping our ice cream. These guys are the real deal. Head to one of their locations for an ice cream sundae that will change the game forever, or, have it delivered. Summer is best celebrated with ice cream in hand so we invite you to join us in making that a priority this summer in Boston.

1. Have a Luxury Picnic with Boston Picnic Co.

Photo Credit: Boston Picnic Co.

If you want to treat yourself and some friends this summer in Boston then you are in for a real treat with Boston Picnic Co. They offer elevated and unique events across New England for every occasion. Their picnic packages are perfect for engagements, bridal showers, baby showers, date nights, birthdays, company outings, or simply enjoying life in the summertime. Each package includes florals, rentals, decor, food, beverages, set up, and pack up. They will deliver and set up your picnic before you and your guests arrive. Once you and your guests arrive, they leave and allow you to fully enjoy the experience during the reserved time. They also take care of all clean up necessary. This epic picnic experience is an absolute must for your 2021 summer of dreams in Boston.