Where To Go in Maine | Long Weekend Itinerary & Things To Do

Maine during shoulder season is exactly the getaway all of us are craving. Picture the perfect fall weekend filled with beautiful foliage, delicious lobster, craft beer, and a short road trip. Think crisp mornings, cozy evenings drinking hot chocolate and shopping, and beautiful afternoons wandering among crunchy leaves under warm sun. It truly is the quintessential trip for a long weekend to soak up all the colors and vibes that remind us of fall. So if this is your first time visiting, here is a list of all of our main Maine must-do’s to make the most of your trip! 🙂

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Continue reading to learn where the best places to go in Maine are and what there is to do there to create the perfect 3-4 day long weekend in Maine!

1. Portland

Portland is a welcoming New England coastal town with views of Casco Bay and a plethora of delicious food options. So if you’re flying in here to start your Maine getaway, be sure to build in a bit of time for it!

Portland Food Scene

If you enjoy freshly caught seafood and delicious homemade pastries, you are in the right place. Here are some of my favorite places to eat & drink: 

• Belleville Bakery —  A small bakery with a great selection of baked goods. The cardamom buns are a must try.
• Moonday Coffee —  Quaint drop-in coffee shop with coffees and teas. The masala chai tea latte was a unique twist that provided a lovely blend of spicy and warm aromas.
• The Holy Donut — A popular, local to Maine donut shop. We had the apple crumble and apple cider cinnamon sugar donut. Delish!
• Cheese Louise — A specialty grilled cheese shop. Great for a quick and easy lunch to grab while exploring.
• Allagash Brewery — for some craft beer, and a delightful tour filled with tastings if you have time.
• The Highroller Lobster Co. — Viral lobster roll restaurant with an eclectic vibe. Absolute must try if you’re in the mood for lobster.

As far as things to do in Portland go, we recommend checking out Portland Head Light. This is a beautiful place to take a stroll and see the stunning Maine coastline. Pro Tip: We recommend getting there closer to when it opens to avoid crowds and get a parking spot. Fort Williams Park is open daily from sunrise to sunset.

Where To Stay in Portland:

• Hotel: The Canopy by Hilton
• Apartment: The West End Retreat

2. Road Trip from Portland to Acadia

Next on the weekend itinerary is a road trip to Acadia! Usually we wouldn’t highlight the travel portion of a trip, but honestly when the views are this good – it’s deserving of it!

We rented a car in Portland and made the approximate 3.5-hour drive north along Route 1 to Bar Harbor and Acadia National Park. We decided to take the scenic route, which took us closer to 8 hours, but it was so worth it!

Pit Stops from Portland to Acadia

We totally get that even the most scenic of drives still need some pit stops to break up the long stretches. There are many beautiful small towns and coastal spots to stop at along the way! Here are some of our favorites: 

• McLoon’s Lobster Shack was our absolute favorite meal the entire trip. This small lobster shack is located on a small island, across from the area’s oldest working lobster wharf. We were going to eat at Red’s Eats by the main road going through Wiscasset, but the experience at McLoon’s was so much better. 

• Marshall Point Lighthouse and Museum has a beautiful view and rocky beach. Fun fact: this lighthouse was in the movie Forrest Gump!

• Camden, ME is the perfect place to stop for a delicious coffee break. We stopped at Zoot Coffee, I had the chai latte and loved it! After, we stopped in a few of the cute local shops.

3. Bar Harbor & Acadia National Park

At the end of our roadtrip we landed in Bar Harbor, a small town on Mount Desert Island that serves as a popular base for those wishing to visit Acadia National Park. We stayed in a beautiful Airbnb in the woods, about 10 minutes away from both downtown Bar Harbor and the main Acadia park entrance. This served as a relaxing retreat after our days hiking in the park 🙂

Acadia National Park – Day 1

On Saturday, we started the day by going to Cadillac Mountain, which is the highest peak on the eastern seaboard. Fun fact, from October through March this is the first place you are able to see the day’s sunrise in the country!

If interested in sunrise, you’ll have to make reservations for your vehicle ahead of time during the busy seasons (late May – October). Typically they will release ~ 30% of reservations 3 months in advance of the travel date, and then will assign the remaining 70% of reservations 48 hours before your travel day.

Unfortunately, we were not able to get sunrise tickets from the website since we went on a such a busy weekend, but even if you aren’t able to get the tickets online there are still other options to get to Cadillac mountain for sunrise! The first option is to hike up Cadillac North Ridge Trail, which is a 4.2 miles out-and-back trail with an 1,128 ft elevation gain. There is also a shuttle that the National Park Service runs, that could get you close to the mountain as well.

After our sunrise hike, we walked along the Jordan Pond Path, which is an easy, serene 3.3 mile loop. We also added in South Bubble, which has about a 500 ft elevation gain with beautiful views of both Jordan Pond and Eagle Lake. If you are looking for souvenirs, the Jordan Pond House has a better selection than the main entrance gift shop in our opinion.

Pro Tip: Get to the park early, the crowds make it difficult to park and explore the park in the afternoon. 

After a lovely day exploring, we went to McKay’s Public House in downtown Bar Harbor for delicious lobster bisque and fish & chips. We then shopped for souvenirs for our friends, and finished the evening by drinking hot chocolate at Choco-Latte Cafe. 

Acadia National Park – Day 2

On Sunday, we hiked The Beehive Loop Trail, The Bowl, and Gorham Mountain, a 2.2-mile loop. Disclaimer: if you have a fear of heights, this trail may not be for you. There are multiple places where you have to climb up a rock face using the metal bars provided. But if you’re cool with that, the climb is worth the beautiful views overlooking Sand Beach, the Atlantic Ocean, and all the colorful fall foliage that Maine is so well known for.

In the afternoon, we then walked along the Ocean Path Trail to Otter Point, including Thunder Hole and Sand Beach. If you are there at the right time, you may be lucky enough to see a seal playing in the water!

At the end of the day, we decided to get ice cream at Mount Desert Island Ice Cream. As a non-dairy ice cream eater, I was thrilled to try a waffle cone with apple cider donut dairy-free ice cream. 

We finished our trip by driving back to Portland and flying out early the next morning. Don’t forget to look at the leaves during take off! 🙂

Where To Stay in Bar Harbor:

• Popular: The Acadia Inn
• Motel: The Bar Harbor Villager
• Hotel: Atlantic Oceanside Hotel & Conference Center

Weekend Map + Drive Route

An overview of the road trip route from Portland to Bar Harbor, where you can get to Acadia National Park, is below. Reminder that it never hurts to take the scenic route – in fact, we recommend it!

About the Author: Tracey is an award winning nurse, cat lover, and hiking fiend who enjoys traveling in her free time & providing firsthand tips for the places she’s been to!

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