Top 10 Things to Do In Portland, Maine

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Looking to book your next vacation? Portland, Maine is a great place for a dreamy trip to a cozy seaside town. We are sharing Top 10 Things to Do in Portland, Maine.

Picture this…it is a cool early morning, the salty air is blowing in from the coast and seagulls are calling above head. You’re strolling down cobblestone streets full of history and sipping on a warm cup of coffee with pastry in hand. You stop at a dock and peer out over calming rocky cliffs and watch the waves roll in over the rocks. You realize this is pure bliss.

Now imagine this dreamy place is real, and it is Portland, ME!

We just took a trip (our first big trip since the pandemic) to Portland Maine and it was the perfect, place to unwind and relax and enjoy the slow flow of the coastal town. The food and sites of this New England town left us wanting to extend our stay a week or two longer. When we landed, we rented a car (highly recommend!) , which gave us the flexibility to explore a lot of Maine’s coast! We visited small towns outside of Portland, like Kennebunkport, Biddeford, Cape Elizebeth, Old Orchard Beach and even took a trip up to Acadia National Park! We have included some of our favorites in this list. Whether you’re going for a couple days or a week long vacation, we have a list of the top 10 attractions and eateries in Portland, Maine.

Why Go to Maine?

Maine offers all the character and cozy feelings!! Portland is Maine’s largest city, without the fast hustle and bustle of a large city. The pace of Old Port in Portland is more tranquil, especially in the morning hours. It is a great retreat on a vacation! Each town in Maine is enveloped with character and history that seem to tell a story of decades and centuries past. The rocky coast line is dotted with lighthouses and land is filled with quaint towns and mountainous forests. There seems to be an ease to the lifestyle of the people of Maine and maybe that has to do with the beauty that surrounds it. After our trip to Maine, we are already planning our next trip back!

What are the best times to Visit Maine?

Maine is gorgeous in the fall, as the forests that cover the state are changing colors to orange, red and yellow. We took our trip right before the peak of the fall colors but the air was starting to get cool. Coming from Dallas, we were pleasantly surprised by the weather in late August. Even though we did just miss the peak of the trees changing color, we feel that that would be the best time to visit Maine. The peak of Maine fall foliage is mid September to mid October.

Top 10 Things to Do in Portland, ME

We have broken down this list into top 5 places to visit and top 5 places to eat! The perfect guide of food and attractions for a trip to Portland.

Eateries in Portland, ME

1. Arabica Coffee Co.

We frequented this coffee shop almost every morning we were in Portland. The coffee and pastries were delicious! Arabica’s aesthetic from the outside gave us Harry Potter vibes, and the atmosphere inside was just as dreamy. We stopped by for a coffee and walked around Old Port several mornings before our day started. It was a perfect stop and close to everything!

2. The Holey Donut

Have you ever had a potato donut? Neither had we!! Holey Donut is a donut shop right off the water in Old Port that serves donuts made from a mashed potato base. Sounds different, but tastes SOOO good. We tried several flavors as we stopped here multiple times as well! It was that good! These donuts didn’t leave a bad sugary taste in your mouth or give you a sugar crash soon after eating. We tried the GF Chocolate Sea Salt, Sweet Potato Coffee Cake, and Cinnamon Blueberry. YUM!

3. Portland Lobster Company

THIS IS. A MUST! Portland Lobster Co was voted the best lobster in 2021 and we have to agree! On the evening we grabbed dinner here, we were starving and it hit the spot That day, we took a day trip to Acadia and didn’t get back to Portland until around 8:00 pm. The restaurant was busy, but the wait for food was SO worth it! The lobster roll was amazing!!

The best lobster roll, Portland Lobster Co.

4. Allison’s (Kennebunkport)

Kennebunkport is a short ride south of Portland. Visiting this quaint town was one of the highlights of our trip. We spent a day here, looking through shops, going to visit Walker’s Point (a gorgeous lookout to George Bush’s compound. That evening we met some friends at an Amazing restaurant. I think we all agreed it was some of the best food we had on the trip. The restaurant has a beautiful and casual atmosphere. Morgan ordered scallops and I ordered the salmon! It was absolutely delish!! Highly recommend! Also, enjoyed it so much I guess I forgot to take pictures!

5. Down Front (Peak’s Island)

After several hours of bike riding around the island and looking at all the sights along the rim of the island, we stopped at Down Front for a scoop of ice cream! The place was so popular there were limited flavors but the ice cream did not disappoint. It hit the spot on this warmer day of bike riding.

Best Places To Go in Portland, ME

1. Old Port:

Old Port is a historic, very walkable section of Portland, packed with gift shops, boutiques, restaurants, coffee shops, and bakeries. Most streets are paved with cobble stone and fits the historic old character of the buildings. We loved exploring all the shops and restaurants in this area. In the mornings, old port is fairly quiet but is busier in the afternoon time. It’s such a cute place to stay and walk around during your visit. Every day we walked around in old port, we seemed to find a new place or street to look around.

Cobble stone street in Old Port Portland, Maine

2. Peaks Island

Peaks Island is a must when visiting Portland! It is a short, inexpensive (I believe it was $8 per adult) fairy ride from Portland. The island gave us major Taylor Swift Folklore vibes! When you arrive on the island, you are met with a couple cute shops and seaside neighborhoods. There is a bike rental shop, Brad’s Bike Rental, a short walk from the fairy port. You can rent bikes for $20 for 3 hours. We rented bikes and rode around the gorgeous Peaks Island loop! We soaked up every bit of it and would say that renting bikes is a must when on the island. It was so much fun to leisurely ride around the island loop and make stops to walk out on the rocks near the ocean. This was our favorite day and was so dreamy!

Stopped for ice cream at Down Front on Peaks Island

3. Kennebunkport

If you take a short 35 minute drive outside of Portland, you will arrive in Kennebunkport. In our opinion another one of our favorite places. This small town outside of Portland, is quiet and quaint with eclectic shops, restaurants, and multiple art studios. Walker’s Point Estate, former president George Bush’s summer home, is just down the road from the square. A road and sidewalk lead to Walkers Point in Kennebunkport making it easily drivable or walkable.

4. Portland Lighthouse at Cape Elizebeth

Maine’s coast is dotted with lighthouses, and Portland Lighthouse at Cape Elizebeth is a popular attraction. The light was built in 1791, making it the oldest lighthouse in Maine. It was in service until 1989. The lighthouse structure is a breathtaking piece of history. On either side of the lighthouse are beautiful overlooks along the rocky coast of Maine. There are trails adjacent to the lighthouse, making for a beautiful walk along the coast.

5. Old Orchard Beach

Old Orchard Beach is a beautiful beach just 25 minutes south of Portland. There is a great restaurant (The Shack) just off the water that we ate dinner at one evening. They had great fish and chips! We spent an evening at Old Orchard Beach eating seafood and walking on the beach. The beach is beautiful. If you’re looking to dip your toes in some sand and jump in some cold ocean waves, this is a great place.