Guide to Portland, ME

We fell in love with this outdoor-centric city, and we hope that we can inspire your future travels to Maine.

We drove up from New Orleans, spent one overnight in CLT rented an all wheel drive car because we were expecting snow storms. Luckily we missed the two blizzards that were heading our way!

When in Portland, we stayed at a cost-effective Inn that was dog friendly and started our next day at the Portland Headlight, then ventured into the city. We highly recommend the following places!

Portland Head Light near Cape Elizabeth

Eventide Oyster Co.’s gluten-free and regular lobster rolls were absolutely incredible! We HIGHLY recommend trying these. They make their own gluten-free buns in house. After grabbing lunch make sure to check out the city and the dock.

One thing that we were happily surprised by was that almost all of the shops were dog friendly. The only places we had trouble going in with our dog Tank was anywhere that serves food or cocktails.

Shops that should be on your list:

  • Fitz & Bennett Home
  • Venn + Maker
  • Campfire Pottery
  • Fitz & Bennett Home
  • Zane Boutique

After shopping we drove around Portland to see their City of Lights and order some dumplings to go. We found some gluten-free dumplings at Empire Chinese Kitchen which is so hard to find!

Day Two:

When the donut is just that GOOD!

We started our day by grabbing some donuts at Holy Donut. They have two separate cases for GF and Regular, even some vegan ones!

Next Stops:

When traveling we are always try to venture out to the suburbs to get a less touristy view and perspective of the area. We wandered through Yarmouth and Falmouth. We were looking for town squares but couldn’t find any. We loved this little market called Town Landing Market. We found some cute local finds, grabbed snacks and headed over to the dock. We also found some blueberry dog treats that our dog Tank LOVED.

After checking out this area we went to Acadia National Park for a sunset hike. Which was STUNNING and goes down as one our favorite National Parks to date. We took the Gordham Mountain Trailhead and got an incredible view! We also walked along Park Loop Rd which had a trail all along the water which was just amazing. If you are planning on going during the winter be sure to check out our guide how to hike in ice and snow. Acadia is also a great spot to view the northern lights, we didn’t stay until after dark but it’s on our list to go back and see if we can spot them!

We drove back to Portland and stopped downtown to grab some dinner to go from three restaurants. This is something we typically do when venturing out to a new city, a takeout night including all of the top dishes. We grabbed a gluten free pizza, kebabs, but loved the whoopie pie we found at the pizza place. It is gluten free and vegan! Fun Fact: Whoopie pies were invented in Maine!

Day Three:

We woke up and grabbed coffee at Coffee ME up, the service and coffee is fantastic there! Next stop Kennebunkport, ME aka KPT! This is now our favorite little town south of Portland.

We highly recommend spending a whole day here. We went to all off the shops, talked to lots of locals, and ate some traditional maine food. We had no problem bringing our large dog with us in the shops. This town center is the absolute vision of New England charm.

We went to the Boathouse for hot cider to warm up and definitely want to visit the restaurant Alisson and Batson River Brewing and Distilling next time we are in town.

Before the sun went down we tried to spot Bush’s house and went to Mother’s Beach just before sunset, which was quite magical.

We can’t wait to check out more beaches in this area come August! After getting our dose of Vitamin Sea we decided to look at some Christmas lights local to the Kennebunkport area then dine at Old Vines Wine Bar. The restaurant and wine bar had a tent set up for winter which was heated and if you make reservations you can request a spot by the fire. I loved their cabernet sauvignon, merlot was great, and Jeff had some beer. Their food was also pretty delicious, we ordered a filet, fish with broccolini, and some apps.

Day Four:

We started our day on the road heading to White Mountain National Forest which is on the border of New Hampshire and Maine. It’s a must see in our books! We hiked a trail along a creek and it was gorgeous! Definitely want to spend a whole day here next time to explore all of the views.

After having a lovely hike in the mountains we drove to Portsmouth, NH. We wanted to explore more of this state after seeing all of the gorgeous views.

We went to the town square and hope to plan a whole trip dedicated to Portsmouth, NH. The shops were very cute, the desert shops were our favorite, and the small city was beautiful at night. Make sure to grab a cappuccino and ice cream macaroni next time you’re here. If you’re here in the fall or have a hankering for a caramel apple head to Kilwins for their apple pie caramel apple. It’s one of our favorites. This town was less dog friendly than Portland but definitely worth a trip and not just a visit. The states motto is Live Free or Die and this is something we whole heartedly agree with. Love to love your life and live freely.

Out trip is almost at it’s end, we grabbed our last dinner at DiMillios in Portland. We HIGHLY recommend going and grabbing their Lazy Lobster Admiral’s Portion (which was out of the shell) and their jumbo shrimp which is priced per shrimp and it’s because they’re HUGE! I actually loved the shrimp more and Jeff’s favorite was the lobster. Honestly, the best shrimp I’ve ever had and it’s one of my absolute favorites.

Thank you for reading our blog! This was by far one of our favorite trips. Stay tuned for our next trip out there in August!

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