Boston Fall Trip: Where to go, where to eat, what to do

Nothing beats a fall roadtrip! I've been wanting to go to Boston for some time now and decided fall was just the perfect season to go! Initially, my plan was to go to Boston for 2 days and then Providence for our last day but I wasn't able to leave the city for 3 full nights. But if you can, Providence is definitely a cute town to stop by for more cute cafes, food and beautiful architecture!

Where to Stay

Let's be honest, Boston hotels are expensive and so are airbnbs! But I found this super cool hotel that is a lot more affordable than most places and is still in a prime location! The Revolution hotel is a boutique hotel located on Berkeley st. and they offer loft style rooms, rooms with bathrooms down the hall or in your room. This hostel style hotel is what allows it to come at a cheaper cost. We stayed in their loft style rooms which are located across the street from the main building. This was such a beautiful room and although it wasn't the cheapest one available it was well worth the price!

What to Do

Walk around Beacon Hill

This is a must stop neighborhood for your next photoshoot in Boston! From the beautiful Acorn St, to Myrtle St., to Louisburge Square, to Cedar Lane Way and finally to the famous Rouvalis Flowers shop, there are so many nice places in this neighborhood. Check out this website for the perfect walking tour itinerary.

Walk around in Harvard Yard

I feel like this is a classic must do when in Boston! Head your way to Harvard Yard and enjoy just walking around the stunning University. As well, this is where the OG L.A. Burdick is located so you can grab a hot chocolate there before walking around! A classic for me for sure!.

Walk around North End

Another great tourist attraction! I love exploring around the Quincy Market and North End for fun local shops as well as beautiful architecture!

Shop at the coolest bookstore: Brattle Book Shop

One of my favorite discoveries! This cute bookstore actually uses the alley beside their store as an extension of their existing location! I found so many cool vintage books to add to my collection and got some cute photos as well!

Where to Eat

coffee shops and Brunch

1. Contessa

Located on the rooftop of a hotel on Newbury St., this stunning italian restaurant is most definitely a must stop! Their dinner menu is really expensive so going for breakfast is a great way to save some money while enjoying this stunning location!

2. Tatte Bakery

Probably one of the most popular coffee shops in Boston, one you can't miss! Not only is there so many locations around the city but the aesthetics are definitely worthwhile! We got the prosciutto and Parmesan Scrambled eggs as well as Peach Ricotta Tartine (seasonal). They were both super yummy and not to expensive! They are known for their Shakshuka so I would definitely try that next time I go. They also offer a variety of pastry at the counter! Everything looked simply delicious!

3. George Howell

After having visited the Brattle Book Shop you can stop by George Howell for a little energy refill! If you are a fan of latte art, this is a must go to!

4. Gracenote

The perfect little espresso stop on your way to North End! This coffee shop has no seats but is so cute for a little on the go caffeine break!

5. L.A. Burdick

With many locations around Boston, you definitely have to try at least 1 hot chocolate during your visit! From white, to milk, to dark chocolate they have everything you could ever have dreamed of! As well, if you go anywhere near a celebration (Halloween, Christmas...) they have some themed specialty chocolates for the occasion! If you are craving a little something to eat, grab a piece of their Linzer Torte and thank me later!

6. Blue Bottle Coffee

Although I didn't have the chance to go on my 2 day escapade, this is a classic coffee shop I go to whenever in New York or LA! Definitely one of my fav coffee chains in the US. The minimalist style and coffee itself makes it worth the trip to one of their many locations in Boston.

Dinner and drinks

1. Ciao Roma

The perfect spot for a romantic date night! A roman inspired Italian Restaurant located in the heart of Boston’s historic North End! The building itself is worth a visit, looks like it was taken straight out of Disney World haha! The inside of the resto is just as cute and the service was incredible! We had mentioned we were celebrating our anniversary and they offered us a glass of prosecco as well as a special printed menu which said happy anniversary! Although it's nothing super exceptional it is such a lovely attention to detail! And of course, the food was amazing, that squash burrata... to die for!

2. Trade

This newly renovated restaurant was another stunning location! The cuisine offered is a mix of Greek and Mediterranean flavors which felt different from everything we ate so far in Boston. The service was once again amazing, the server was so nice and let me choose whichever table I wanted since he saw I was taking photos! We got their burger & autumn salad and both were simply delicious! (The seasoning on their fries... yummm.. I want that spice mix!!)

3. Terra

If you've been reading for long enough you very well know, whenever there's an Eataly, I will be there! Terra is their rooftop italian grill dinning offering! During the summer months they have an outdoor lounge seating area but the inside is definitely the star of the show and off course, the pasta is always a garanteed win!

Bon Appetit & Safe Travels!


Megan Chartrand-Robichaud

September 11, 2023