Celebrating Fall in New England – 4 Days in Maine

There’s something charming and romantic about New England in the fall.  The ocean crashes against the rocky shoreline while the leaves put on a colorful display across the countryside. The days are crisp, perfect for warm drinks, plaid blankets and cozy evenings by the fire. It’s always been my idea of a perfect weekend to close out summer before the long, cold days of winter.

Ben and I finally decided to plan a trip this year, and it did not disappoint! New England is a region in the Northeastern part of the country that includes 6 states: Connecticut, Maine, Massachusetts, New Hampshire, Rhode Island and Vermont.  The Pilgrims, fleeing religious persecution in England, began settling in this region in 1620, and the history and culture are apparent throughout.

For reasons unknown, I’ve always been drawn to Maine the most (although Rhode Island and Vermont are close seconds). Maine has almost 3,500 miles of coastline – more than California! – and over 3,000 off-shore islands. It is the perfect starting point to explore this beautiful part of the USA!


Celebrating Fall in New England – 4 Days in Maine

4 days, 4 nights

  • Day 1 – Drive from Boston to Bar Harbor along Coastal Highway Route 1
  • Day 2 – Acadia National Park & Bar Harbor
  • Day 3 – Sunrise in Acadia & Sailing in Portland
  • Day 4 – Exploring Portland

If you have extra time:

  • If you like to hike and/or camp, spend some extra time in Acadia National Park. With mountains, forests and ocean, there is so much to explore.  Spend an extra day or two hiking in Acadia or check out one of the several campgrounds that can be reserved in advance.
  • Check out Portland’s many sites including the Portland Museum of Art, the observatory, and Casco Bay. Portland also has a great food and drink scene. We could have easily spent another day or two here.

Tips for a great trip:

  • Before our trip, we had no idea that both Bar Harbor and Portland are common stops in Maine for cruise ships. The number of cruise ships in port can have major impacts on how busy the city is, so consider checking the schedules before picking dates for your trip. You find schedules and the number of passengers on each ship here and here for Bar Harbor and Portland, respectively.
  • Acadia National Park receives more than 2 million visits each year, and the park can be very busy during peak times. To avoid the lines when you enter the park, purchase your pass online and print it before your trip. Visitors must pay an entrance fee of $25 per vehicle from May to October, and the pass is good for 7 days.
  • If you own an I-Pass or E-ZPass, take it with you. There are a lot of toll roads between Boston and Bar Harbor, and rental car companies will charge an extra fee to use theirs.
  • If you plan to stay in a Bed & Breakfast during your trip,  book early. We booked our trip a couple of months in advance and had a difficult time finding an available, affordable room in Bar Harbor.


Maine Coastal Highway U.S. 1

Day 1 – Drive from Boston to Bar Harbor along Coastal Highway Route 1

There are two main ways to get to Bar Harbor from Boston by car. The fastest route takes 4.5-5 hours along Interstate 95. The slower route follows Coastal Highway U.S. 1 along the Atlantic Ocean past small villages, beautiful lighthouses, lobster pounds and antique shops.

You can spend as little or as much time as you’d like exploring this highway, but we recommend giving yourself the full day. We spent almost 11 hours on the journey and didn’t even stop at all of the places on our list! Here’s a look at our favorite stops along the way.


Points of Interest Along Coastal Highway U.S. 1

Nubble Lighthouse – Our first stop outside Boston, Nubble Lighthouse is located in York, Maine. The beautiful lighthouse is situated a few hundred feet offshore atop a rocky island. No one has lived on the island since 1987 when the light was automated, but you’ll still find a line strung from the mainland to the island. A bucket was hung on the line and used by light keepers to cross back and forth up until a few years ago when it was blown off during a storm.

If it’s not too early in the day, spend time exploring York, one of Maine’s most popular vacation destinations.

Nubble Lighthouse

Kennebunkport – Less than an hour up U.S. 1, Kennebunkport is a great place to park the car and explore on foot. There are lots of shops along the main strip.  Grab coffee on the patio at Mornings in Paris or drinks on the Spirit of Massachusetts. If you’re ready to dive into some seafood, check out The Clam Shack.


L.L. Bean Flagship Store – If you’d like to do some shopping stop at the L.L. Bean Flagship Store in Freeport. You’ll find everything outdoors related here, as well as an outlet store across the street.

The Ocean Roll – If you’re ready for another snack, don’t miss The Ocean Roll! This vintage food truck serves fried clams, lobster rolls, chowder and more. Place your order at the window and grab a seat at the picnic tables outside.

Ocean Roll

Arundel Flea Market – You’ll want to arrive early to find the best deals at this flea market. It’s located next to the Arundel Antique Village and just down the road from The Ocean Roll.

Seashore Trolley Museum – We stumbled upon this museum after leaving the flea market and thought it was such a unique find! The Seashore Trolley Museum is the oldest and largest mass museum of mass transit vehicles in the world. For $10 you can tour the museum and ride on several restored streetcars.

Seashore Trolley Museum

Belfast –Belfast wasn’t a planned stop on our route, but we were starving by the time we arrived! We stopped at Three Tides to grab an early dinner on the patio that overlooks the water. The food was delicious, and they serve beer from Marshall Wharf Brewing Company next door. We didn’t get a chance to explore Belfast, but it looked to be worth a stop!

There’s so many other stops to consider along the way based on your interests. We’ve put together a map of our recommendations that we hope you’ll find helpful!

To open the map on your phone in Google Maps, select the star after the title of the map. Open Google Maps and hit the Menu button in the top left corner. Select “Your places”. Scroll down to the bottom and you should find the saved map.

Bar Harbor

We arrived in Bar Harbor fairly late on day 1 to check into our Bed & Breakfast, Holland Inn. A Bed & Breakfast is the preferred accommodation in many of the smaller towns throughout Maine and New England. Nightly rates can quickly get expensive (especially if you don’t book far enough in advance), but we thought Holland Inn was a great value for the money.

Holland Inn

Holland Inn

We stayed in the Parkman, a smaller room with a large patio and private bath. We were only a short walk (~5 minutes) from the ocean, pier, restaurants and shops.

Holland Inn

Holland Inn

Holland Inn

And the best part of staying in a Bed & Breakfast? The breakfast!

Holland Inn

Holland Inn

We finished off day 1 with a stroll through Bar Harbor that ended at Leary’s Landing Irish Pub for a pint. Bar Harbor does not have a great restaurant and bar scene (at least by Chicago standards), but this is one of the more authentic, fun bars we found during our stay.

Day 2 – Acadia National Park & Bar Harbor

After breakfast at Holland Inn, we packed a lunch and headed to Acadia National Park for a full day of hiking. We’ll share a full guide to Acadia soon, but here’s a teaser to how incredibly beautiful and fun our day was!

Acadia National Park

After a very full day of hiking, we headed back to Bar Harbor to shower and find dinner. Good food is fairly limited, but we settled on Mckays Public House after stumbling on their beautiful outdoor patio. We were seated inside and really enjoyed the atmosphere – it’s a great spot for a drink with a date! The food was fairly average though.

We weren’t in Bar Harbor long enough to find great restaurant recommendations, but we heard several people mention Galyn’s. Let us know if you are familiar with any other restaurants in Bar Harbor!

Day 3 – Sunrise in Acadia & Sailing in Portland

Watching the sunrise from the top of Cadillac Mountain is a classic Acadia experience, and we woke up early to beat the crowds! We’ll provide more details on how you can experience it in our upcoming guide to Acadia National Park.

After breakfast, we checked out of Holland Inn and headed to Bass Harbor Head Light. Bass Harbor is a beautiful lighthouse that was built in 1858 right along the cliffs. The house still serves as a private residence for a Coast Guard member and his family, but visitors can walk around the side of the house for a view of the light. Don’t miss the path at the other end of the parking lot that leads down a set of wooden stairs for a great view of the harbor side of the light.

Bass Harbor


From Bass Harbor, it’s a 3 hour drive to Portland where we checked into Marriott’s Courtyard Portland Downtown/Waterfront property. The location is perfect, right on the edge or Portland’s Old Port and Waterfront Districts, and it’s one of the nicest Courtyards I’ve stayed in!

We popped in and out of some shops as we made our way down the pier for a two-hour sunset sail with Portland Schooner Company. Sails are offered several times a day, and guests are able to bring their own food and drinks. We had very little wind during our sail, but it was so fun to experience Maine from the water!

If you’d like to book your own sail, they start at around $38 / person. If Portland Schooner Company doesn’t have availability, check out Maine Sailing Adventure or Casco Bay Lines. You could also rent a kayak for a few years for an active adventure on the water.


After our sail, we went to Novare Res Bier Cafe for a drink before a late dinner at Fore Street. Portland has an amazing food scene and both places were excellent. Novare Res has a great selection of draft and bottled European beers along with food – get the chicken meatballs! Fore Street is one of Portland’s best restaurants, serving amazing seafood with great service.

For another unique restaurant experience, check for reservations at The Well at Jordan’s Farm. The Well is a farm-to-table restaurant situated on a working farm.  They were hosting a wedding the weekend we visited so we weren’t able to try it, but I’ve read amazing reviews.

If you have specific restaurants you want to try while in Portland, be sure to look for reservations well in advance of your trip. They can be hard to come by! Some restaurants will also take walk-in reservations when they open.

Day 4 – Exploring Portland

We woke up to a steady light rain on our last day in Portland, and it didn’t stop until we left! But our first order of business was breakfast at Standard Baking Co They make delicious breads and pastries. We ordered a morning bun, a pumpkin spice scone and a loaf of bread to take home. They’ve released a cook book in recent years that I’ve already requested from the library!

If you love donuts, also check out The Holy Donut. The line was too long when we stopped, but we heard great things about the handmade donuts.

Standard Baking Co

After breakfast we drove around Portland to the Eastern Promenade, a public park and recreation area. It’s a beautiful area for a walk with a 2.1 mile path for walkers and runners. There’s also a beach for swimming in the summer. The rain would not let up, so we did a driving tour of Portland.

We stopped at Fisherman’s Grill for a fresh seafood lunch. This was an amazing little seafood shack that opened at noon with a line out the door. There are only a few tables inside so be prepared to take your food to go if needed.


After lunch, we stopped at Allagash Brewing for a free beer tasting. They also offers free tours of the brewery. They don’t sell additional beer for consumption on site, but you can grab a case to take home with you.

Our last stop before heading back to Boston for our flight was Portland Head Light. The lighthouse is located about 20 minutes from downtown Portland in Fort Williams Park. It’s said to be the most photographed lighthouse in America and the oldest in Maine. The views along the rugged coast were stunning, even in the rain.

Give yourself a couple of hours to explore this park. There’s several trails and sites to explore beyond the lighthouse, and it would make a great spot for a picnic lunch. There’s also a museum inside the lighthouse you can visit for a few dollars.



Visiting Maine in the fall is one of my favorite trips from recent years. The landscape is stunning, and there is so much to do and see. Have you ever been to Maine? Where’s your favorite place to experience fall?

2 thoughts on “Celebrating Fall in New England – 4 Days in Maine

    • We were a little early for peak colors, but it was beautiful. I was blown away by Maine – there was so much to do! We’d love to go back and spend more time in Acadia and go camping. Sounds like you have a trip to add for next year! 😉

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