Fun Restaurants in Boston + What to Order

 

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One of the best things to do in Boston is…eat? You better believe it is, absolutely! The problem I had in Boston wasn’t finding delicious places to eat. Nope, instead, my issue was finding enough time in a week to try them all! Sadly, I ran out of time. However, I did my best to eat my way through this New England city. In the process, I wound up finding some fun restaurants in Boston you should try!

Ready…set…GO!

Fun Restaurants in Boston

1 | Tatte Bakery & Cafe

Located on Boylston Street near the Boston Public Garden, Tatte Bakery & Cafe was my first stop after checking into my pre-conference hotel.

I got the Prosciutto & Fig Pannini and it was excellent! I paired it with the Mint Lemonade which is made fresh daily with all-natural sweeteners and has just the right balance of sweet and tart. I’m not a fan of either of these extremes so for me, it was perfect and worth its $4.50 price tag.

2 | Boston Burger Company

Another good eatery located on Bolyston Street (but down near Fenway Park), the Boston Burger Company is a must-try for those who love both traditional burgers and those with fancy elevations!

I got The Sophie burger with prosciutto, goat cheese, candied walnuts, fig jam, mixed greens tossed with lemon vinaigrette and a balsamic reduction. While it came with the choice of homemade potato chips and either baked beans or coleslaw, I gave that all up and got sweet potato fries instead. Absolutely great choice because they were amazing just like the burger!

You might be seeing a theme forming here and yes, I do love the whole fig/prosciutto/goat cheese combination. I highly recommend this different take on a traditional burger.

I love this…it’s definitely me!

3 | Roxy’s Grilled Cheese & Burgers

On my walk from my conference hotel to explore Harvard, I stopped at Roxy’s Grilled Cheese. I’m not going to lie. I’m like a kid when it comes to grilled cheese sandwiches. I absolutely adore them and they are a go-to comfort food for me.

The interesting thing with Roxy’s is that it was started by a college student as Boston’s first food truck. There were licenses for food carts but trucks at that time were illegal. The owner got a food cart license after bugging city officials and became the first food truck to park on a Boston city street. It is now a brick and mortar and still operates its food truck!

Once again, this is a restaurant known for taking a common favorite and elevating it in many different ways. And in keeping with my theme, you guessed it…I got The Allston which had herb goat cheese, arugula, caramelized onions, and fig jam.

This very well may have been the best grilled cheese sandwich I’ve ever had in my entire life. That’s saying a lot because I have had countless grilled cheese sandwiches!

Heads up! They have POUTINE! Yes…a Canadian favorite and one you can really only find in certain places in the northern United States. I said “yes, please” and I dug into the maple brook farm cheese curds and beef gravy like it was the last meal on earth!

4 | Union Square Donuts

So…I’m not a huge fan of donuts. In fact, I’m fairly picky. I love Krispy Kreme and I hate Dunkin’ Donuts. That right there is going to spark controversy with some. But, I do love trying unique flavors of donuts when I travel or finding ones that are uniquely decorated.

This is exactly the reason I put Union Square Donuts on my list. After all, it IS an award-winning donut company! Their daily, handmade-from-scratch donuts originate from brioche dough and they also make all of their own glazes, jams, and creams!

I got the Maple Bacon and it was my favorite by far. It features real Vermont maple syrup and is topped with thick, smoky bacon. That sweet and salty tickled my tastebuds!

However, I couldn’t pass up the Boston Cream since Union Square’s is considered the city’s official donut. The official donut and the official state dessert all-in-one? Don’t mind if I do!

5 | Winsor Dim Sum Café

Any fans of dim sum out there? If so, I have the place for you in Boston. The Winsor Dim Sum Café has excellent, authentic dim sum. It had good ratings so I decided to try it out.

My main requirement for dim sum? It has to have amazing pork buns and Winsor had them. It’s my favorite part of the entire dim sum experience.

I added steamed shrimp dumplings and fried veggie spring rolls to complete my order

6 | Flour Bakery & Cafe

Flour Bakery & Cafe was a place I had heard so much about prior to my arrival in Boston. It was on my list to try for their Boston Cream Pie. It’s a bustling, lively bakery with a menu much more extensive than the famous dessert.

I had the Applewood-Smoked Bacon Sandwich with arugula, tomato, mayo served on focaccia toast. I got this without the bacon and served on white untoasted bread. It was good but nothing memorable honestly. This verdict will become quite interesting a little ways down.

The Boston Cream Pie was absolutely fantastic and what I think of as the kind most people are familiar with. Layers of cake with pudding-texture cream topped with luxurious chocolate!

My friend got the Blackberry Cupcake and let me take a photo. She thoroughly enjoyed it and I thought it was quite pretty!

7 | Stephanie’s On Newbury

In case you’re wondering, this is what dining with travel bloggers looks like!

Stephanie’s on Newbury is a highly popular restaurant located on Boston’s Newbury Street in the popular Back Bay area. Indoor/outdoor seating is available and it’s the perfect location for a summer dinner with the girls!

I got the Lobster Pot Pie which is a delicious New England take on the chicken pot pie. Can you say heaven? I love lobster and highly recommend this dish if you visit!

The Lobster Roll is also a great choice!

For dessert, I shared a Boston Cream Pie with my friend. It is not your typical Boston cream pie and is even served with chocolate to pour on top. I appreciated the difference and it will always stick out in my mind for this reason. And yes, it was yummy…in a lava cake kind of way!

8 | Dirty Water Dough Company

Some nights, you just want a good ol’ slice of pizza. But, you don’t want to sit down and order or have a long wait, right? I ducked into Dirty Water Dough Company to grab a quick slice one night when I found myself in this exact mood. Thankfully, it was close to my conference hotel!

As sliced pizza goes, it’s pretty yummy! The interior was really cute and the friendly, fast service didn’t hurt either!

9 | Parish Cafe

A neighbor to Tatte Bakery, you have to have a meal at Parish Cafe. As is with a lot of Boston’s cafes, it is an indoor/outdoor eatery with a creative menu. The unique take on the creative? The menu features sandwiches created by different chefs around Boston!

I ordered The Flour B.L.T. which is the creation of Chef Joanne Chang from Flour Bakery. It featured applewood smoked bacon, tomato confit, bibb lettuce, basil mayo, texas toast and was served with potato chips.

Did I like it? Yes. Why should this stand out? It’s a BLT. True. Please understand, I am not a bacon fan (cue gasps everywhere, I know!). I typically order anything with bacon sans bacon. Something told me to leave the bacon on this order and I’m glad I did. It was soft bacon with a deep savory flavor that I loved. The tomato confit and basil mayo were perfect complements!

Tying together my earlier mention of an interesting verdict from Flour Bakery. I found this version, the Flour B.L.T. which came from a Flour Bakery chef, much better than the Flour Bakery’s actual Applewood Smoked Bacon Sandwich.

10 | Map Room Tea Lounge

I can’t remember exactly when I first heard that you could have afternoon tea at the Boston Public Library. It was after I had arrived in Boston. I just recall booking at fast as I could after finding out. It’s no secret that I love afternoon tea…especially when it’s in a cool atmosphere like the Map Room Tea Lounge!

Located within the historic McKim Building of the Boston Public Library, the Map Room is Boston’s first tea-inspired bar and lounge.

I booked the Copley Tea Service which is only served on the weekends and is $48 for adults. This includes a soup or salad in addition to the regular tea service. For $6 extra, consider adding on a featured iced tea. I got the Blood Orange Hibiscus (orange peel, pomegranate, lemon) and it was very refreshing after I added sweetener!

For my hot tea, I chose Blue Flower Earl Grey. From Sri Lanka, it features a classic caramel-flavored Ceylon tea with sweet citrusy bergamot and blue cornflower petals. It was right up my alley. The good thing is you are able to try multiple teas so you don’t have to pick just one!

Summer Strawberry Salad with a Citrus Poppyseed Dressing

On the double-tiered tray were savory sandwiches on top with the sweet stuff on the bottom. Plain and currant scones were served on a side plate with blood orange preserves, lemon curd, and Devonshire cream.

Savories included Maine Lobster, Egg Salad, Chicken Salad, Smoked Salmon, Virginia Ham, and English Cucumber. I traded out that last one for another Main Lobster. I don’t do cucumber whatsoever!

The sweets consisted of Blueberry Cobbler, Zucchini Cake, Lemon Thumbprints, Chocolate Sinclairs, and Macarons.

11 | Blackbird Doughnuts

Here’s another cool donut shop you have to swing by! Blackbird Doughnuts serves both donuts, crafted teas, soft-serve ice cream, and even a few ice cream novelties!

I had the yummy Lychee Ginger Lemonade Doughnut with the regular black iced tea. Hit the spot on a warm summer day after walking the city. The menu changes seasonally with the exception of a few year-round staples such as The Blackbird and the Everything Bagel Doughnut. Yeah, let that one sink in!

12 | Double Chin

Double Chin is another later night place my friends and I hit up after shooting some night photography of Boston. I ordered the Pork Dumplings with ginger soy sauce as I only wanted a snack at that time.

The story here is that I left behind an expensive pair of sunglasses. I was unaware they had fallen out of my backpack at some point. It was the next day when I realized I didn’t have them. I traced my steps and came up with dinner being the only place it could have happened. I called and they found them in almost the same place I was sitting. This meant someone had moved them but didn’t take them. I picked them up that night and profusely thanked the manager that held them for me!

13 | Regina Pizzeria

Regina Pizzeria is known as Boston’s original pizzeria. They have been greeting patrons with “Welcome to Boston’s Original Pizzeria!” since 1926. There are multiple locations, but the North End location is the original and the most famous. It almost always has a line out the door!

I waited in that line for a little while and then had to step out due to time constraints. Later in the week, I wound up visiting the Fenway Park location after a tour.

When trying new pizza for the first time, I always get pepperoni. Not only do I like it but it allows me to be able to compare everyone’s pizza as evenly as possible. Regina’s is outstanding. Absolutely fantastic. Top-tier.

I’m going to leave you with this: Make a beeline for Regina’s.

Boston Cream Pie-More Fun Restaurants in Boston

Of course, I’m not going to leave out Boston’s famous dessert and the official state dessert of Massachusetts. Along with the already mentioned Flour Bakery & Cafe and Stephanie’s On Newbury, go to the following restaurants to get the best Boston Cream Pie in Boston!

14 | The Last Hurrah

The Last Hurrah at the Omni Parker House may be known for its Boston Cream Pie but it also has the best martini list I have ever seen anywhere ever in my travels! The owner creates all of his own and even based one off his trip to the Reyka Factory in Iceland! I got the Cherry Blossom and asked to add the two frozen grapes from the Prickly. A sugar rim and cherry liqueur added to the inside of the glass rounded out the perfect martini!

15 | Modern Pastry

Another place to try a form of Boston Cream Pie, Modern Pastry was one of my favorites. However, its menu features many more items including Boston Red Sox cookies.

16 | Mike’s Pastry

Located diagonally across the street from Modern Pastry is Mike’s Pastry. They also have the famous dessert but offer many other delightful treats.

MAP IT!

Where to Stay in Boston

Travel Insurance

Don’t forget your travel insurance. Protect yourself and your trip. With World Nomads, which is what I use, you can get a free quote!

PIN IT!

Who’s hungry? I am! I’ve brought myself back to Boston via dreamy food memories. Now, it’s time for you to make your own! Hit up these fun restaurants in Boston and more if you have time. The good thing is it’s really nice in the summertime and an easily walkable city which should help you be able to eat more!

Have you tried any of the fun restaurants in Boston? Which one was your favorite or the one you would like to try most? Let me know below!

‘Til next time…

Trimm Travels,

Heather