Weekend Guide to Portsmouth, NH & Portland, ME

08/30/2017 21 Comments

There is nothing like the New England coast. It varies from state to state, with each one offering it’s own style to the New England name. Here is my guide to experience two of the most picturesque cities in New Hampshire and Maine, with a few stops a long the way ;-).

Day 1

Kittery, Maine

What to Eat:  Chauncey Creek Lobster Pier

What to do: Kittery Trading Post & Outlets

Right outside of Portsmouth is a great place to pick up anything you may need to enjoy the outdoors on the east coast. The outlets are a great place to pick up some new outfits too 🙂

Portsmouth, New Hampshire

What to do: Check out the historic North Church that was the center of colonial Portsmouth & Market Square for some shopping.

Happy Hour: Portsmouth Brewery

Dinner: Row 34 was a highlight of the trip! It’s an oyster bar offering small plates and craft beer with a sleek modern style.

Day 2

Portsmouth, NH

What to do: Your own walking tour! The city is small enough to explore on your own. Take a stroll down Bow St to browse the shops and restaurants. Make your way to Harbor Marina and Memorial Bridge to watch the boats passing by under the draw bridge. Finish your tour taking in Marcy street and ending in Prescott Park.

Where to Eat: Annabelle’s. Ice cream in the am?! Dessert First 😉

Portland, ME

What to do: Take a walk downtown along the wharf.

Lunch: Boone’s Fish House & Oyster Room has a great outdoor patio to enjoy some fish tacos and a beer.

What to do: Book a Portland Discovery Cruise to take in the lighthouses and Portland from the water.

Dinner: Street & Co along a cobble stone alley known as the old port on Wharf Street. I highly suggest ordering the Lobster Diavalo for two!!

Day 3

Portland, ME

Where to Eat: Arabacia Coffee

Grab a nitro brew coffee and egg sandwich to fuel up for the day at Arabacia Coffee. It has a really open warehouse vibe inside.

What to do: Allagash Brewing Company, Foundation Brewing Company

Both brewing companies are within walking distance to each other, whether you park at one or the other. Allagash is a beautiful outdoor/indoor set up with free tastings of 4 different 3oz beers. You can purchase beer to take home, but there is no beer available to drink on site.  They also have a Bite into Maine’s food truck available with lobster rolls that are to die for! Tip: Order your lobster roll picnic style, it was heaven 🙂

Cape Elizabeth, ME

What to do: Two Lights State Park & Portland Head Lighthouse

Spend the afternoon on the sandy but cold beach in Two Lights State Park. TIP: It’s $8 per non maine resident in the car.

Back to Portland, ME

Dinner at Old Port Sea Grill

Finish off the weekend with some homemade ice cream at Captain Sam’s!

I’m ready to do this weekend all over again!!


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California Globetrotter

Cupcake N Dreams

New Yorker blogging about travel and lifestyle things that make me happy!


  1. Reply



    How fun!! Thanks for sharing this as I have been wanting to do a day trip to Portsmouth. It looks like so much fun.

    • Reply

      Cupcake N Dreams


      Definitely recommend Portsmouth Marie! I want to go back and explore more!

  2. Reply



    I’ve never visited these states (they are on my bucket list) and this post makes me REALLY want to visit them!!!!

    • Reply

      Cupcake N Dreams


      I feel you Erin, I still have a few states left on mine!

  3. Reply

    Jessi's Design


    SO much fun! I would totally be down for visiting here! xo

    • Reply

      Cupcake N Dreams


      I think you and the family would enjoy it!!

  4. Reply



    So glad you guys made it to Row34! We have one in Boston and it’s delicious! I’m drooling over all your food – seriously it’s so good! Glad you had a great time! xo, Biana

    • Reply

      Cupcake N Dreams


      I am so happy we did too! John was raving about it because he had been to that one before. I wish I took better pictures, but the ambience in there was too dark for them lol.

  5. Reply



    You had me a Lobster Roll and food truck! I would love to fill up before heading to the state park. Can you go in the lighthouse?! I love exploring old lighthouses! Always looking for things to do when we visit each state, so this is super helpful! #wanderfulwednesday

  6. Reply

    Marcella ~ WhatAWonderfulWorld


    Oooh, so many delicious looking eats! YUM! Cape Elizabeth looks really lovely too, you captured some great skies when you were there!

  7. Reply



    Mmm…I’m loving the sound of all that ice cream. Sounds like you had a great weekend; thanks for all the recommendations!


  8. Reply

    Ruth | Tanama Tales


    It is clear that you guys ate like royalty. That lobster looks fantastic! I have never experienced the New England Coast. I know I have to plan a road trip around the area one day. #wanderfulwednesday

  9. Reply

    California Globetrotter


    Looks like yet another cute town! Although I feel like I’ve seen that lighthouse before!! #WanderfulWednesday

  10. Reply

    Cathy (MummyTravels)


    How gorgeous! I haven’t quite made it that far north on the east coast but it always looks so beautiful – I do love a good lighthouse and coast city, plus the seafood sounds amazing. Thanks for linking up with #citytripping

  11. Reply

    Erica @ Whimsical September


    Oh this post just made me SO nostalgic! I visited this area of New England back in 2011, and I quickly (!) fell head over heels in love. Walking around Portsmouth was such a dream. Such a beautiful part of the country!

  12. Reply

    Ava Meena


    This looks like a great itinerary! I’m planning a trip to New England next spring and this is definitely useful, thank you! #TheWeeklyPostcard

  13. Reply



    I haven’t really spent a lot of time in New England since I was a teenager…but it’s really been on my radar for a road trip with the family! Your meals look divine…and we’re all about a sweet treat! #theweeklypostcard

  14. Reply

    Nancy @ NY Foodie Family


    What a great looking trip. I’m loving all the tasty eats and drinks! I’m due for another trip to Portland, Maine, since my husband and I were last there years ago, pre-kids. I’ve never been to New Hampshire yet, but hope to go soon. #theweeklypostcard

  15. Reply

    Vanessa Brune


    New England certainly seems to have tons to offer when it comes to good cuisine! I’ve always wanted to visit the area and the cape looks like a lovely spot that I have to put on my bucket list now!

  16. Reply

    California Globetrotter


    Portsmouth looks like a lovely little each coast town! I’d love to start exploring more of the east coast, but I don’t think I’ll get very far with all this delicious food! Thanks for linking up with #TheWeeklyPostcard!

  17. Reply



    Ahhh this looks like a perfect weekend! I’ve only visited a tiny part of New England, but it looks like a really great place to live (except in winter, maybe. I can’t deal with the cold!). Feeling hungry now looking at all that food!