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Friends Having Breakfast

A Day Away | Pies, Pies, Pies

Updated: Nov 14, 2023

By 4Squares Residential Group in Partnership with Judi 411

Well, Thanksgiving time is here! As the world opens up again and we gather around the

table, all eyes are on what's on the menu. For us at 4Squares, we are here for all the

fixings, but most importantly, we are here for pie!

Check out some of our favorites near and far. Warning: you will be hungry when you're

done reading this list!

Petsi Pies, 285 Beacon Street, Somerville, MA

Look no further than the next town over for scrumptious, flaky-crusted pies with equally

fantastic fillings at Petsi Pies. Voted Best of Boston for 2021, the only difficulty with

Petsi Pies is deciding which one to eat. Thanksgiving seasonal selections include the

classics: Apple, Apple Crumb, Sweet Potato, and Pumpkin, but if you’re feeling

decadent, don’t pass up the signature Chocolate Bourbon Pecan.

Holiday order cutoff is November 15th. As they say at Petsi’s, “We don’t want you to be

without pie, so get your order in!”

Drive-By Pies, 248 Cypress Street, Brookline, MA

Drive-By Pies started as a back-porch pie pick-up in Reading and now is a thriving

business and a household name in Brookline and beyond. Featuring sweet and savory

pies as well as breakfast, lunch, and a freezer of pies to go, Drive-By Pies is gearing up

for Pie-Eating Palooza and taking online orders until 5 pm on November 16th.

Gluten-Free Alert: the gluten-free folks will be happy to know that Drive-By Pies offers

GF Blueberry, Cherry, Pumpkin, and Pecan pies as well! No one will be left pie-less if

Drive-By Pies has anything to say about it. Be grateful. Give Thanks. Eat Pie. Sounds like Thanksgiving to us!

Montilio’s Bakery, locations in Quincy, Brockton, Braintree, and Weymouth

Are your Thanksgiving travels taking you southbound beyond the gas tank on 93? If

you’re on deck for bringing dessert, then order your pie from Montilio’s and grab it on

the way! Well-known for their cakes, Montilio’s makes equally yummy pies, including

their epic Boston Cream Pie and Ricotta Pie, as well as traditional Apple, Pumpkin, and

Sweet Potato pie.

Fun Fact for Dinnertime Trivia: Montilio’s Baking Company’s cakes were served at

JFK and Jackie’s wedding, the Inaugural Balls of JFK, Ronald Reagan, and George

H.W. Bush, and most notably TO THE POPE!

Florence Pie Bar, 17 Main Street, Florence, MA, 413-341-3283

Families heading westbound for the holiday will want to make a pit stop at Florence Pie

Bar for comfort food distraction. Housed in a converted general store, the vintage charm

of Florence Pie Bar is a perfect complement to their farm-fresh menu of seasonally

inspired fruit pies, cream pies, quiches, meat pies, and hand pies. If you’re up for a

more avant-garde holiday pie offering, consider ordering the Lemon Chess or Salted

Chocolate Pie (or both!). Orders close on November 17th and can be placed online or

by phone.

How about you? What are you looking forward to most this holiday season? Whether it’s

food-related or you’re curious where to shop this season, 4 Squares has your back.

Contact us via and share your thoughts, suggestions, and questions! Want more? Subscribe to our newsletter!

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