2 In Like A Local/ North America/ United States of America

Best Things To Do In Boston – A Local’s Insider Tips & Travel Guide

Last updated on Jun 26, 2018

This week’s edition of Like a Local is brought to you by Kristin and Tom, the authors of Picnic Wednesday. In this guide they will cover all the best things to do, places to see, where to eat and off the beaten track activities to do in Boston, Massachusetts. If you’re planning a trip to Boston and want to get all the insider local tips, this is the post for you!

Hi Kristin and Tom, tell us a bit about yourself! What city do you feel like a local in?

Hello! We are Kristin and Tom from Picnic Wednesday. We began our website while we were living in Boston. We both had crazy, hectic jobs in the corporate world. We started having picnics every Wednesday to get away from the mundane work day and see more of our city (like a local)! Hence our website’s birth.

Through our picnics, we fell in love with our city. We started road tripping around New England and also fell in love with travel. We both left our jobs and now are in Mexico City taking an intensive Spanish course. When we travel, we LOVE reading blog posts to help us travel like a local.

How long did you live there for?

We lived in Boston for about three years. Although we weren’t born and raised in the area, we jam packed every weekend wandering around the city and discovering new things to do. We quickly settled into life like a local in Boston.

What are your favourite places to eat?

The pizza and Italian food in Boston is world class. Historically, Boston has a large Italian population that brought along their food and culture from overseas. We made an entire map marking the best pizza spots in Boston.

Some of our favorites are Santarpios in East Boston, Regina Pizzeria in the North End, Galleria Umberto in the North End, and Pino’s in Brighton.

For Italian food, the North End is the place to go! Our favorite spot is Panza. It is a small, cozy place but can get PACKED on weekends. Entrees run from about 12USD – 18 USD but the portion sizes are huge. They also have extremely cheap bottles of wine for the area (starting at 20 USD).

The North End Boston, photo by Picnic Wednesday

The North End Boston, photo by Picnic Wednesday

After a large Italian feast, head to Modern Pastry or Mike’s Pastry for a cannoli. Chocolate dipped with traditional ricotta filling is our favorite. Bostonians have an ongoing feud about which one is better, but we love them both!

Do you have a favourite place to study or work?

Yes, the courtyard of the Boston Public Library in Copley Square. The BPL draws tourists and locals alike because of its historic façade and classic interior. Grab a chair in the courtyard and enjoy the ambience and free wifi.

What about when you want to relax? Do you have a favourite relaxing spot?

The Boston Public Garden and Arnold Arboretum are two of our favorites. The Boston Public Garden is a in the center of the city, right next to the historic Boston Common. There is a picturesque draw bridge and swan boats where you can leisurely ride around the small pond.

Boston Public Garden, photo by Picnic Wednesday

Arnold Arboretum in the Jamaica Plain neighborhood is a large nature reserve with some beautiful overlooks of the city. The Samuel Adams brewery is also in Jamaica Plain. Some beer and the arboretum would make for a fun travel day!

Is there a typical activity locals do in their free time?

In the summer, locals love to go on weekend roadtrips, especially to Cape Cod, or “the Cape,” where many people have beach houses. Our personal favorite place for a weekend roadtrip is Portland, Maine.

Portland Head Light, photo by Picnic Wednesday

Portland Head Light, photo by Picnic Wednesday

Portland has lighthouses, great seafood, and tons of breweries. What could be better?! Read more about some of our roadtrip recommendations here.

What is your favourite activity or thing to do in Boston?

Our favorite thing to do, aside from picnicking, is to frequent the craft beer breweries. Even if you don’t love beer, many of the breweries have great food and a really cool vibe! Similar to our pizza map, we made a craft beer map here.

Breweries and food trucks, photo by Picnic Wednesday

Breweries and food trucks, photo by Picnic Wednesday

Do you have a favourite photo spot?

Yes! Any of the historic sites along the Freedom Trail. The Freedom Trail features sites from the Revolutionary War time period, when the US was still a British Colony. To walk the Freedom Trail, you follow the red bricks throughout downtown. You can see all of the sites within a 2 mile (about 3.5 kilometer) walk!

The U.S.S. Constitution (oldest naval ship still in the U.S. fleet), Paul Revere’s house in the North End, and the Bunker Hill Monument are some of our favorites. Walking the freedom trail is truly a can’t miss!

When is the best time to visit Boston?

Boston is COLD in the winter and the summer is usually pretty packed with tourists. We recommend early fall (September or October). The leaves are changing colors and the weather is still wonderful!

What’s one “touristy” thing in Boston everyone should actually do?

Along with the Freedom Trail (described above), walk around the historic neighborhood called Beacon Hill. This neighborhood has picturesque brick row houses. Check out the street pictured below called “Acorn Street.”

Acorn Street, photo by Picnic Wednesday

Acorn Street, photo by Picnic Wednesday

Also, go to a Boston Redsox baseball game. They are a ton of fun and the best part is getting to party in the Fenway area with all of the die hard fans!

What’s one “off the beaten track” place people don’t normally know about but should know about?

Boston’s Chinatown doesn’t get a ton of credit compared to New York and San Francisco, but there is some great food and good photo ops!

Chinatown Boston, photo by Picnic Wednesday

Chinatown Boston, photo by Picnic Wednesday

We are obsessed with a restaurant called Gourmet Dumpling House. They serve some awesome Szechuan food. The place gets packs so get there around 11:30AM before the lunch rush!

Any tips or tricks on how to navigate Boston?

Boston’s MBTA system (called the “T”) is great to zip you between all of the tourist areas and nearby neighborhoods. We definitely don’t recommend renting a car unless you are planning on roadtripping throughout New England.

Any tips on how to visit Boston like a local so that travellers reading this can blend in?

If you want to look like a local in Boston, Massachusetts, we recommend going to a sports game of any type. Boston loves their sports teams and thinks that they are the best in the world. Cheer for the local teams and you’ll blend right in!

What is the best area in Boston to stay in? Any specific hotels you can recommend?

We recommend staying in the Copley Square area, specifically at the Fairmont Copley. It’s a beautiful area with good restaurant options and walking distance to most tourist attractions.

If you’re looking for an AirBNB, we recommend looking in Brookline or Cambridge. You will truly feel like a local in those areas. They’re safe, close to the center of the city, and more residential.

Find the best hotel deals in Boston here.


What do you love most about Boston?

We LOVE how much people worship nice weather. Since winter is long and dreary, people spend all of the summer and fall outside and enjoying the city! It’s such a wonderful time to be in Boston. Nothing compares!

Anything else you want to share about Boston?

Boston, Massachusetts is a wonderful place. It is quintessentially American with its history and heritage. For a big city, it is extremely walkable, which is one of the things that we love! It’s the perfect city for tourists who want to live like a local.

If you have any questions or want any more recommendations, we would love to hear from you at picnicwednedsay@gmail.com. Also, please visit our site at picnicwednesday.com for more information and follow us on social media! Thank you for reading and happy picnicking!

Boston travel guides worth checking out:

DK Eyewitness Travel Guide Boston
List Price:$20.00
You Save:$5.00
Price Disclaimer
Lonely Planet Boston (Travel Guide)
List Price:$19.99
You Save:$6.55
Price Disclaimer
Frommer's Boston day by day
List Price:$13.95
You Save:$1.13
Price Disclaimer

Have you been to Boston before? How did you find it? Let us know in the comments below! I hope you find this guide useful in planning your trip to Boston and to experience the city like a local. If you’re planning a family trip to Boston, check out the best things to do in Boston with kids.

Enjoyed reading about the best things to do in Boston from a local? Pin it!

Planning a trip to Boston? Find out everything you need to know with this local's travel guide. Including the best places to eat, typical activities locals do in their free time, off the beaten track places to discover and much more! #boston #unitedstatesofamerica #usa #likealocal #traveladvice #travellikealocal

Planning a trip to Boston? Find out everything you need to know with this local's travel guide. Including the best places to eat, typical activities locals do in their free time, off the beaten track places to discover and much more! #boston #unitedstatesofamerica #usa #likealocal #traveladvice #travellikealocal

Planning a trip to Boston? Find out everything you need to know with this local's travel guide. Including the best places to eat, typical activities locals do in their free time, off the beaten track places to discover and much more! #boston #unitedstatesofamerica #usa #likealocal #traveladvice #travellikealocal

About the author

Hi! We are Kristin and Tom from picnicwednesday.com. We started our site a year ago when we developed our passion for having picnics around Boston, Massachusetts. We expanded our weekly picnics to other parts of New England, USA. After traveling extensively around the USA, we headed to Latin America to study Spanish and expand our horizons! Right now, we are in Mexico City enjoying the warm sun and tacos galore!

Website | Instagram | Twitter

Kristin and Tom, authors of Picnic Wednesday

Kristin and Tom, authors of Picnic Wednesday

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  • Reply
    Kristin D.
    June 6, 2018 at 4:23 pm

    Greta! Thank you so much for featuring us in your series. We hope that this inspires people to visit Boston. We truly love it there!

    • Reply
      June 7, 2018 at 6:24 am

      Hi Kristin, thank you for being part of it! You’ve definitely inspired me, I’ll be adding Boston to my next USA road trip bucket list!

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