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An Awesome Maine Getaway: Portland, Bar Harbor and Acadia

ByKasia Kalemba Hours
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One of the best things you can do on the East Coast during the fall is to explore New England during its most beautiful season of the area, fall! Nothing compares to the crispy air, changing leaf colors, local seafood, and just the most beautiful nature all around. I have visited Maine twice during this magical time and I hope this guide makes you save this post for a future getaway as well. The following itinerary is built for a 3-5 day trip to two of Maine’s amazing areas: Portland and Bar Harbor with Acadia.

While these destinations are one of the best things to do in Maine in the fall, winter is also a magical time in town, and visiting in spring will save you from the crowds.

And don’t worry, if you’re not a hiker, you can explore most of the area from your car! Of course, the best views are rewarded by some effort but don’t fret, I’ll share spots with you that you can drive up to and not sacrifice the view 🙂

Don’t forget to save the map at the bottom of this guide!

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Quick Maine Logistics

  • Since l live on the East Coast, when I went on this awesome Maine getaway, I drove to all my destinations. If you’re not from the area, you can fly into Portland, Maine, and rent a car there. It will be difficult to explore the area without one.
  • September and October are the best months to visit Maine but an early November or even Christmas visit will save you from the peak season crowds. Don’t forget spring either before the summer crowds start flocking in.
  • A lot of businesses are seasonal being closed between mid-November to mid-April. Check the hours before heading out!
  • Weather is very important to check when visiting especially if you want to spend time outdoors. We got one full day of rain forcing us to stay inside and needing to extend the trip by one more night!
  • Speaking of the weather, pack accordingly! You will be pretty high up north so the temperatures might be slightly more chill than what you’re expecting!

Now, let’s get to your Perfect Fall Maine Getaway

My itinerary below can be done in 3-4 days depending on how much time you’d like to dedicate to the outdoor activities. I would recommend spending a full day in Portland and then the remaining in Bar Harbor and Acadia. These two cities are located about 3 hours from each other but depending on your in-between spots along the scenic drive, that time can be longer.

A Day in Portland

Portland deserves at least a day of your attention. It’s such a charming town lined with cobblestone streets, brick buildings, small shops, harbor views, and delicious food. Walking around them fills my soul with happiness and I promise it will fill yours too! Here is a day plan of things to see in Portland, Maine:

Portland Lighthouse

Portland Head Lighthouse is located a short drive from the city center. I’d recommend going there first thing in the morning to avoid the crowds and enjoy the area before it gets busy. But before you reach this picturesque gem, stop by Omi’s Coffee Shop for coffee and breakfast. It’s on the way to the lighthouse and they serve some delicious food!

When you get to the lighthouse, spend some time walking the small trails around and soaking in some sweet ocean views. If you’re into visiting lighthouses, you can enter this one during the season. Don’t forget to walk around though and get a view of the lighthouse from a distance.

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Allagash Brewery

For any beer fans, make your way toward Allagash! It was founded in Maine and the brewery is pretty awesome. While you will have to drive a little outside the city, it will be worth it! There are other breweries nearby too if you want to do a little brewery hopping like Geary Brewing Co or Foundation Brewing. If you’re driving there, you can also grab this to-go!

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Old Port & Commerical Street

For the early afternoon, the Old Port, Commercial, and Exchange Street are the areas of town to walk around and soak in the vibes of Portland. You’ll find many small shops, boutiques, famous bookstores, coffee shops and restaurants, and those charming cobblestone streets. My favorite spots are all the ones that have waterfront views. There is something about boats and port cities that always gets me. Plan to spend at least half a day there exploring and eating!

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Here are some food & drink spots to check out:

  • Portland Lobster & Co: This place is iconic for a reason. Often, touristy and popular places don’t live up to their expectations but I have visited this place on two different trips and it was delicious! Can’t miss a stop here during your Maine getaway.
  • DiMillo’s On The Water: This is another popular spot in the area but don’t worry, the food and the views are spot on!
  • Flatbread Company: Since I am a big fan of anything pizza-related, I had to stop at this place. It did not disappoint! They have great outdoor seating right on the water!
  • The Highroller Lobster: I was really excited to try this place. Don’t get me wrong, it was good, but it was a very pricey lunch and the lobster rolls were kinda average.
  • Duckfat: Fries fired in duckfat? Sign me up!
  • The Holy Donut or Hifi Donuts: Looking to satisfy your sweet cravings? Look no further with these perfect creations.
  • The Bramhall: A nice speakeasy with some fancy cocktails for an after-dinner treat.
  • Rosie’s Pub: I liked this spot for a late-night beer. The vibe was a little more local and it was the perfect chill pub atmosphere.
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Eastern Promenade and/or Peaks Island

Eastern Promenade is a cute waterfront area for a walk or a nice picnic. The park has some romantic sailboat views and is just a pleasant place to spend some time in.

Visiting Peaks Island might be a stretch for one day in Portland but if your Maine getaway is a little longer, consider taking a short ferry ride there. Here is a quick and informative guide from Annaleise’s blog if you decide to visit this cute little gem of a destination.

Portland to Bar Harbor Drive

Now on to the next part! If you love Portland, you will LOVE Bar Harbor. Although it’s much smaller, it’s nonetheless stunning. A drive from Portland to Bar Harbor is about 3 hours but if you want to make a half-a-day adventure out of it, here are some spots to consider along your Maine getaway route. Depending on how much time you have, you can stop in all of them or choose one as they offer similar vibes.

  • Freeport: Your first stop is known for its LL Bean flagship store, sweet shopping streets, and small-town charm.
  • Wiscasset: Called the Prettiest Village in Maine, this small town is known for Red’s Eats, a famous lobster roll spot.
  • Camden: Another charming little town on your Portland to Bar Harbor drive. Check out Harbor Park, for some pretty water views or Mount Battie for from above views! NYT wrote a cool piece on this spot with a short itinerary for a visit.
  • Blue Hill: A low-key spot offering the best views without the crowds. You won’t find many things to do here but the point of this detour is to experience a small off-beaten path route and small-town life. If you make a stop here, you’re now under an hour away from Bar Harbor!
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Exploring Bar Harbor

Bar Harbor is one of my favorite towns on the East Coast despite being a pretty touristy spot. Located right on the water, this gateway to Acadia is just the perfect place for a fall in Maine getaway!

Since it’s a pretty popular vacation town, you have many choices for your accommodation. I stayed at Atlantic Eyrie Lodge and LOVED the views from there. Other good places in the area are Acadia Inn, Bar Harbor Motel, and Bar Harbor Cottages and Suites.

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You can spend a whole day just enjoying the town and here are some highlights not to miss:

Main Street & Agamont Park

Bar Harbor’s Main Street is great. You’ll find tons of shops, restaurants, bars, and the entryway into Acadia! It’s likely you’ll have a meal and a snack there. A really pretty spot off of Main Street is Agamont Park. It may be small but the views are great. You can spend time watching boats pass by and people-watching.

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Bar Island

Bar Island may seem like a small uninteresting island close to the mainland but what makes this place worth seeing is crossing it via a land bridge! As the low tide comes in, you’ll see swarms of people crossing the harbor on foot to explore the island! Don’t forget to check the times of the low tide because if you get stuck there on a high one, you’ll either have to wait for 10+ hr for the next one or have to be rescued for a hefty fee 🙂

Food

Bar Harbor has some delicious food, especially seafood. It would honestly be a sin if you didn’t try some there. Keep in mind that a lot of restaurants are seasonal so check before heading out! While the food isn’t outrageous, it is pricey due to its prime tourist location. It’s hard to go wrong as most places will serve good food but here are some top-rated recommendations:

  • Stewman’s Lobster Pound: Located right on the water, this spot will likely have a long queue to enter! We stopped there for some beers which happened to have blueberries in it! The views were amazing and the vibes are the definition of Bar Harbor!
  • Side Street Cafe: You’ll find this gem a couple of blocks away from the action but it’s consistently a top-rated spot in the area. It’s a more casual place with burgers, sandwiches, and lobsters of course.
  • Geddy’s: This spot was one of my favorites in the area and it’s located right on Main Street! Also a pub vibe with some tasty food!
  • Mainely Meat BBQ at Atlantic Brewing: You’ll have to drive a little to get to this gem because it’s located outside the city. However, this spot was amazing and so worth it! Note that there are two locations and I personally like this one in conjunction with the brewery.

For a more detailed food guide, I recommend visiting PackMoreIntoLife post on Bar Harbor eats! I love their recommendations and they even list spots that are open all year round!

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Best Spots of Acadia

If you ended up in Bar Harbor, there is no way you should miss seeing Acadia National Park. Even if it’s for the sole reason that this area of the country doesn’t have that many of them. But before we get into the details of what to see, I’d like to preface that this guide is not for a very active hiker. It’s a more laid-back one although I will throw a more challenging route there for ya. Here are the spots that you should see at the very minimum:

Cadillac Moutain

This spot is the poster child for Acadia tourism. It’s where the US first sees the sun between late fall and early spring. People come here for sunrise or sunset and if you don’t feel like climbing it, well guess what, you can easily drive to the peak 🙂 Certain times of the year also require vehicle registrations. Here is the official info.

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Park Loop Road

Park Loop Road is a great way to see the highlights of Acadia. This 27-mile journey will take you around the park without having to leave the car. Don’t forget to get your park pass as you are not allowed to drive the road without it.

As you’re driving through it, don’t miss the Sand Beach stop from which you can take a short and flat the Great Head Trail. Another known spot is a Thunder Hole, which is a rock inlet in which the waves crash with a big boom sound.

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Beehive or Precipice Trail

There are many hiking trails in Acadia but one of the most known ones are the Beehive and Precipice Trails. The Beehive isn’t easy due to its steepness and spots where you have to climb metal rungs. I am personally not a hiker but took on the challenge and loved it. However, it is certainly not for everyone. The Precipice is very difficult but it’s on many people’s bucket list!

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Jordan Pond

Jordan Pond is a quick 1 hour 3-mile loop trail with stunning views of the pond! The water is crazy clear and so worth the stop!

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Long Pond

Long Pond is a short drive away from Bar Harbor but it’s worth your trip if you love kayaking. It’s such a peaceful area and you’ll love the views from there.

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A Map for Your Maine Getaway

Final Thoughts

I love Maine and I know you will too. Although the best time for a Maine getaway is fall, I’d recommend seeing it in the winter too and in spring as the tourist towns slowly start to wake up. You’ll need at the very minimum 3 days to see some highlights but if I were you, I’d certainly make it at least 5.

Which spots are your favorite? Comment below!

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Kasia is a travel blogger that loves to share her detailed itineraries and travel tips with her community. She's traveled to numerous countries and makes it a priority to explore her home state of New Jersey while still being passionate about her 9-5 career.

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