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  • Writer's pictureDarci Lou

The Ultimate Fall Day Trip From Boston

Updated: Mar 14, 2019

I am going to warn you right off the bat.. This is quite an ambitious day trip, but I do not regret it one bit. You get to be in three different states in one day and have a really pretty view along the way. I made this trip before the trees started turning but I can only imagine that this is a wonderful fall foliage trip as well!

Start in Boston and drive to Salem

This first stop is pretty close to Boston making it a great place to have breakfast or a nice brunch.

I recommend going to Gula Gula! I was able to try the Brie & Apple Sandwich and The King. The Brie and Apple has some of the best Brie I have ever had and is a great brunch option. The King is a classic peanut butter and jelly with a twist! The banana and bacon take the simple classic to a whole new level.

There is some wicked cool art all over this place! Make sure you go to the bathroom area to see some weird but awesome illustrations!

Eating here leads you right into the shops which are a lot of fun to browse through. My favorite ones were The Coven’s Cottage and Wynnots Wands. Wynnots is magical. You can surely find the right wand for you here and the Coven’s Cottage is great for gathering all your potion making needs!

The next stop on the list is about a two hour drive up to Portland, Maine.

This is a cute town to walk around,browse in some shops and have a late lunch or dinner with some fresh seafood. The scallops at the Kings Head Pub were delectable!

Now to turn around back towards home! Set your GPS for Portsmouth, New Hampshire for the last stop on the trip.

Here I recommend getting some ice cream at Kilwins or grabbing a drink in one of the many hopping bars around the cute downtown area. If you make it in time, there are also lots of cool shops and restaurants to explore!

This could easily turn into a fun weekend trip by staying in Maine or New Hampshire for a night or two! I wanted to leave this post really open because this trip was fun because we did not have a strict plan. I hope you can take the bones of my trip and make it spectacular in your own way! Now get going and have a lovely weekend. Remember to subscribe!



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Hey there! My name is Darci and  I created this blog with the hopes of inspiring others.


I am a photographer, designer, baker and avid traveler. You can find all my adventures, my random thoughts on life, and everything in between here! I hope you enjoy this blog as much as I love making it. Have a lovely day!

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