Every summer, I make a Summer Bucket List of things I want to do, places I want to go, and restaurants I want to eat at. This becomes my de facto list of the best things summer in Massachusetts (and New England at large) has to offer. Part usual suspects and part hidden gems, crafting my Summer Bucket List acts as a means of survival throughout the dark winter months.

Despite 12+ consecutive weeks of rain on the weekends this year, I have to remain optimistic that at some point this summer in New England, we will have a nice, warm and sunny weekend day. At which point, I’ll have to tackle my entire Summer Bucket List.

BYOB Sunset Dinner at Sesuit Harbor Cafe in Dennis

A short drive from Brewster (check out my Brewster Neighborohooding Guide), this seasonal clam shack on the harbor in Dennis is always packed with lines snaking through the parking lot. While it’s easier to grab a seat as a smaller party of two, the real fun comes when you go as a group who takes BYOB incredibly seriously. Grabbing some canned beer or seltzers is for amateurs; the real Sesuit pros are shaking up cocktails and pouring them into real martini glasses… while seated at an outdoor picnic table eating fried clams off a paper plate.

Host a Backyard Hibachi Dinner

You can bring in a hibachi chef for your own Benihana-at-home experience.

Martha’s Vineyard Day Trip from Wood’s Hole

Having been to Nantucket several times, it’s a little weird that I’ve never been to Martha’s Vineyard. I’d like to change that this summer, by taking advantage of the $21 round-trip ferry from Wood’s Hole.

Reggie’s Annual Photo at The Canteen in Provincetown

It’s not summer without a trip to Provincetown to take Reggie’s annual summer portrait out back at The Canteen. We’ve done this every year since he was born in 2017.

Westerly Pops Weekend in Rhode Island

I always visit my sister in Westerly during the summer to hit the beach and some of my favorite spots around town (Westerly Neighbhorhooding Guide!), but I’ve yet to time it right for the Westerly Pops, a weekend of music in the park right downtown.

Recreate Blank Street’s Iced Strawberry Shortcake Matcha at Home

Thankfully there isn’t a Blank Street near my home or office, or I’d be spending $100 on iced matcha every week. I’m making it a summer goal to recreate this drink at home, using this Love & Lemons recipe or this TikTok one.

Spicy Shrimp Pizza, Jerk Chicken & Cojitos at Roht Marine

A riverside clam shack & bar on the North River between Scituate and Marshfield, Roht Marine makes the best coconut mojitos (aka cojitos) and spicy shrimp pizza. If you’re driving by in the afternoon and smell jerk chicken on the grill, don’t miss it.

Afternoon at the Raw Bar in Duxbury

Where else can you have your dog try caviar? I’m a big fan of this outdoor raw bar with counter service and a bar.

Weekend in Montreal

Everyone agrees that the best time to be in Montreal is during the summer. Between F1, the jazz fest, Just for Laughs and the film fest, the city is buzzing nearly every weekend and the streets are lined with sidewalk terrasses. I only spent one summer living in Montreal while studying at McGill, but it was a memorable one spent biking around the city, drinking spritzes on the sidewalk and absolutely butchering the French language while waiting tables in Westmount. Now that dogs are allowed on the metro and most terrasses, I want to make it up for a weekend with Reggie.

Drink a Goombay Smash at the Beachcomber

Worth a detour from 6A to Cahoon Hollow for a drink and some very cool merch.

Eat a Maria’s Sub at the Lighthouse

Whether you sit in your car or make it out onto one of the jetties in Scituate Harbor, the Lighthouse is where the OGs like to dine.