A coastal Maine road trip

Happy Wednesday and welcome back to Roadtripper,

The newsletter that’s never “there yet” no matter how many times the back seat asks.

As a former backseat driver on many road trips, I'm sure I probably owe my parents an apology.

We moved around a handful of times as I was growing up, and I didn’t always take to the changes kindly.

In fact, I got to a point where, in response to some of the moves, I – the ever dramatic teenager – suggested: Why don’t we just move to Maine! (Apparently, the most remote place I could think of at 13 years old).

It became a refrain that I used when I was at my brattiest – which isn’t fair to Maine, honestly.

So, while I’m doling out apologies, I feel I ought to give ‘Vacationland’ a fair chance, if only to make up for the years spent badmouthing somewhere I’d never actually been. 🤦‍♀️

With that in mind, let’s take a trip to Maine! 🚗💨

• 🚗 The Route Report: Cruising up the coastline

• ✅ The Check-In: Where to redeem and earn points

• 🛑 The Pit Stop Poll: Passenger Roll Call

🚗 The Route Report: Cruising up the coastline

While there’s undoubtedly more to the entire state, I wanted to experience some of the best that Maine has to offer – so this route is a coastal cruise northbound, largely sticking to Route 1 before ending in Acadia National Park.

Getting there

If you aren’t based in New England, there are a few options for starting this road trip.

For a shorter, more convenient drive, look for flights into Bangor International Airport (BGR) or Portland International Jetport (PWM), possibly requiring connecting flights depending on your destination.

Or you can fly into Boston Logan International Airport (BOS) and turn it into a proper road trip — this option might make for a slightly longer trip, but you will often save big time on flights and car rentals.

How long to spend there

If you only have 3-4 days, flights to BGR might help you make the most of the Bar Harbor/Acadia National Park area.

5-7 days allow you to make your way up from Boston, but with minimal time for extra stops.

A longer trip gives you time to dive a little deeper into the coastal region and all it has to offer.

When to go

The best months? July – October (August is peak tourism season)

Warmer weather means the trails are all open, but it’s not too hot here, giving visitors the perfect escape from the scorching temps other areas experience in late summer. 

Because of that, Bar Harbor is a happening spot, and that’s reflected in higher prices, crowds, and parking spot hunger games. 🫢 

The fall months make for a more balanced experience, with waning crowds while seasonal spots are still open. And the foliage in October is a don’t-miss highlight that draws the crowds back before everything quiets down for the winter.

The Route

Because I love a good flight deal and hate to skip over all the sights, this route starts in Boston.

You can jump in the car upon arrival and head north or book a couple of nights in Boston... if that’s your cup of tea. 🥁😉 

Now, if you have limited days, I’d head straight to Portland. But if time is on your side, there are so many small coastal towns worth exploring along the southern coast of Maine.

• Cape Neddick – for a postcard-worthy view of Nubble Lighthouse

• Ogunquit – for beaches and the Marginal Way cliff walk

• Kennebunkport – for award-winning lobster rolls, Goat Island Lighthouse, and more beaches.

• Cape Elizabeth – for Two Lights State Park and Fort Williams Park to see the most photographed lighthouse in the US, Portland Head Light.

Portland, Maine

Portland, ME is just under two hours from Boston and a great place to break up the drive as you take time to explore more of the coast.

It also pairs well with Cape Elizabeth, only 20 minutes away, and is worth a night or two all on its own.

From the cobblestone streets in Old Port and the stroll-worthy Eastern Promenade, to the working waterfront, Victorian houses, local breweries and renowned culinary scene – Portland packs quite the punch despite being a smaller city.

A few local favs worth checking out:

• Duckfat – poutine fries you’ll dream about

• Eventide Oyster Co. – oysters and more lobster rolls

• Allagash Brewing – local craft brews with family-friendly outdoor space

• The Holey Donut – gourmet potato donuts

• Bread & Friends – bakery and coffee one-stop shop in downtown

• Bite Into Maine – Cape Elizabeth lobster roll spot

Honestly, I’m hungry just thinking about Portland now – if that’s you, maybe opt for a whole food tour?

Back on the Road

After a couple of nights in Portland, you’ll head north again, where there are more coastal towns worth checking out:

• Wiscasset – “Prettiest Village in Maine” and more award-winning lobster rolls.

• Freeport – home to the L.L. Bean flagship store

• Boothbay Harbor – Coastal Botanical Garden and boat cruises

• Rockland – Farnsworth Art Museum and the Maine Lighthouse Museum

• Camden – drive/hike Mount Battie or charter sailing schooners

Plus, more lighthouses and lobster shacks.

As you approach our destination of Bar Harbor, you can take the Acadia All-American Road, a 40-mile scenic byway that runs from Trenton, Maine, through Acadia National Park itself.

This route can become congested in July and August as visitors flock to Bar Harbor and the park, but it’s a drive that is a destination all its own.

Bar Harbor and Acadia National Park

The drive from Trenton brings you into Bar Harbor, the waterfront town that hugs Frenchman’s Bay and serves as the jumping-off point for Acadia National Park.

Historically a summer getaway for the East Coast elite in the Gilded Age, it’s now a hot spot for nature lovers.

What to do there

Whether you’re seeking a luxury coastal getaway or an outdoor adventure, Bar Harbor is the place.

Easy walks along the Shore Path or Bar Island Trail (at low tide), whale watching or puffin spotting cruises, sea kayaking, plus over 150 miles of hiking in the park.

The Acadia All-American Road takes you along Park Loop Road to some of the trailheads and past several of the must-see sights in Acadia National Park, including:

• Jordan Pond – a popular pristine lake with a restaurant famous for its popovers

• Sand Beach — large stretch of sandy beach, great for a chilly swim

• Thunder Hole — viewing area to watch waves crash through the rocks

• Carriage Roads — wide crushed granite paths free of car traffic, allowing visitors to hike, bike, or take a carriage ride to various viewpoints around the park

• Cadillac Mountain – the turnoff for the summit road connects to the Park Loop, but a separate timed reservation is required to drive this route in May-October

If you want to get out of the car and really explore, you can pick from one of many hiking trails. There’s easygoing Ocean Path, the advanced Beehive Trail, the vertical climb of Precipice Trail, and more.

Or head to the quieter side of Acadia for fewer crowds and hike the easy Ship Harbor Trail, explore Southwest Harbor, visit Bass Harbor Head Lighthouse, and more.

✅ The Check-In: Where to redeem and earn points

A trip to Bar Harbor can certainly add up – what with a car rental, park admission, hotels and the pounds of lobster you’ll consume.

So, if you’re looking to make room in the budget, here are a few options bookable with points:

Portland:

• Hyatt Place Portland Downtown – Old Port Square: 20,000-25,000 points

• Courtyard by Marriott Portland Downtown/Waterfront: Starting at 49,000 points

• Aloft by Marriott Portland Downtown Waterfront: 37,000 points

• Canopy by Hilton Portland Waterfront: starting at 44,000 points

• Hilton Garden Inn Portland Downtown Waterfront: starting at 33,000 points

• Holiday Inn Portland-By-the-Bay (IHG): starting at 17,000 points

Bar Harbor Area

• Holiday Inn Resort Bar Harbor (IHG): from 31,000 points

• Hampton Inn Bar Harbor: from 100,000 points

• Under Canvas Acadia (Hyatt): from 24,250 points

For unique stays in coastal towns along the way:

Hyatt’s partnership with Mr. & Mrs. Smith means these cute cottages and former captain’s mansions turned inns are up for grabs with points!

• Blue Bird Ocean Point Inn (Hyatt) – starting at 20,000 points a night

• Awol Kennebunkport (Hyatt) – Starting at 40,000 points a night

• Kennebunkport Captains Collection (Hyatt) – Starting at 44,000 points a night

Where I’d earn points on this trip

Sometimes my preferred stay or the coolest option isn’t bookable with points, and that’s where I switch gears to focus on earning the most points with my booking.

For example, the Bar Harbor Inn comes highly recommended, and the Salt Cottages look like the perfect luxury-meets-cute cottage resort stay, but neither are bookable with points.

If you hold a card that comes with hotel credits like this one, this one, or this one, they can be a handy option for booking local boutique inns, resorts, or seaside motels with the credit and earning 4-10x points on whatever the credit doesn’t cover.

Or if you prefer vacation rentals, there are some really unique options like this cute cottage or this treehouse! 👀

If you go that route, consider using a card like this one – it earns 3x points on vacation rentals.

And there’s always the option to book one of the many campsites in and around the park if that’s more your speed.

In that case, this card earns you a flat 2x miles on everything, from your campsite to park admission to the lobster rolls you eat along the way.

🛑 The Pit Stop Poll: Passenger Roll Call

Whew, I feel like my teenage conscience is clear now, and I also might have a new lobster roll obsession.

Did you know you can fly with a live lobster? Just in case you want a fun souvenir. 🦞

Anywaaays, hope you enjoyed the route and I’ll see y’all next week!

Katie Begnoche
Writer, Daily Drop
29.7604° N , 95.3698° W

With contributions by Sam Anthony.