How to see Maine by train in 4 magnificent nights

Too often when you live in one place, you discount traveling to other parts of the country because it can feel:

"too far away."

"too expensive."

"too hard to plan."

"too full of unknowns."

“like it will take too many days to get there and back.”

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See Maine by train in 4 nights, ThoseCrazyNelsons.com

See Maine by train in 4 nights, ThoseCrazyNelsons.com

If that sounds like you, can I stretch your traveling brain for just a second and recommend a bucket list trip to the gorgeous coast of Maine? Maine's MidCoast and Maine Beaches Association brought us in to discover how easy exploring Maine by train really is. And I’m going to fill you in on all the juicy details.

Photo cred:  Maine’s MidCoast

Photo cred: Maine’s MidCoast

This article is going to:

-provide the answer to “is Amtrak’s Downeaster train from Boston a good way to see Maine?”

-tell you what’s cool in Kennebunkport, Maine.

-show you how to make this a 2-night getaway, if you don’t have 4-nights to spare.

-reveal the friendliest and the safest towns in Maine

-highlight the best lobster fishing cruise in Maine and give you ALL the details on how to eat the FRESHEST lobster you’ve ever had.

-show you a gorgeous picture of Maine’s most photographed lighthouse.

Here's the scoop on what a Maine train vacation would entail. Your trip begins in Boston.

We took a direct flight from Nashville’s airport (BNA) to Boston’s Logan International (BOS), which was pretty painless. When we arrived at the Boston airport, we took a 10-minute Uber ride to Boston’s North Station.

See Maine by train in 4 nights, Amtrak’s Downeaster pics

See Maine by train in 4 nights, Amtrak’s Downeaster pics

What train would you take?

Amtrak's Downeaster train from Boston to Brunswick will take you up the coast of Maine so you can explore a few select coastal cities. The Downeaster train is very comfortable: think business-class seats on an airplane, wide and spacious.

Does the Amtrak Downeaster have wifi?

Yes, so, you ARE able to get work done, although we suggest staring out the window at the passing sights, or visiting the snack car.

See Maine by train in 4 nights, Amtrak’s Downeaster pics

See Maine by train in 4 nights, Amtrak’s Downeaster pics

Where does the Amtrak Downeaster stop?

The Downeaster train schedule offers multiple train departures a day. It goes from Boston to Brunswick with stops in between like: Wells, Portland, and Freeport.

What do Amtrak's Downeaster train tickets cost?

Downeaster tickets are about $60 roundtrip from Boston to Brunswick, but Amtrak does offer discounts and deals; check for these!

Is Amtrak's Downeaster train from Boston a good way to see Maine?

Let's face it, we have a lot to coordinate when we're traveling to a new place. Being able to step aboard a train while it whisks us to our next stop makes for one less worry while vacationing.

See Maine by train in 4 nights

See Maine by train in 4 nights

Night one, your first stop.

Wells, the friendliest town in Maine, was our first stop on the train, but it’s not where we spent the night.

From Wells, we needed a car to get the 25 minutes from the Wells Train Station to the Kennebunks area (where we did spend the night).

Tip: Enterprise Rent-a-Car is nearby and can actually pick you up at the Wells Train Station!

Hello, meet the Kennebunks.

After a day of travel, we finally made it to our first night’s destination: Kennebunk, Maine, the safest town in the state.

See Maine by train in 4 nights, via ThoseCrazyNelsons.com

See Maine by train in 4 nights, via ThoseCrazyNelsons.com

There is another nearby town called Kennebunkport, famous for being the location of the Bush Family residence, called Walker’s Point. (Here are directions to the Bush compound in Kennebunkport.)

See Maine by train in 4 nights, Boathouse Restaurant, Kennebunkport

See Maine by train in 4 nights, Boathouse Restaurant, Kennebunkport

Don’t make this mistake.

When you arrive, you'll think Kennebunk and Kennebunkport are interchangeable terms, but they are not. Two, small beachside villages separated by a teeny bridge, Kennebunk and Kennebunkport are neighbors and are often referred to together as the Kennebunks.

See Maine by train in 4 nights, Kennebunkport, Maine

See Maine by train in 4 nights, Kennebunkport, Maine

Aside from the postcard view of Cape-Cod styled houses along Maine's rocky coast, the Kennebunks area is a coastal resort town that has generations of families returning each year.

Beaches in Kennebunk

Mother's Beach

Kennebunk Beach

Gooch’s Beach

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See Maine by train in 4 nights, where to stay in the Kennebunk area

See Maine by train in 4 nights, where to stay in the Kennebunk area


Need a road trip getaway instead? Try this.


Where to stay in Kennebunk?

You’re not going to stay in a chain hotel here, no siree. There are gorgeous Kennebunk and Kennebunkport, Maine, hotels, inns, and bed and breakfasts from which to choose. We recommend these two properties when planning your Kennebunkport lodging options:

1.The Grand Hotel

A few yards from Kennebunkport, The Grand Hotel is officially in Kennebunk, and is the epitome of New England elegance. The lobby houses an art gallery, so be sure to stop by.

2. Kennebunkport Inn

Kennebunkport Inn is luxury and charm rolled into one historic property.

Kennebunk and Kennebunkport restaurants are amazing, too. Try these.

Mornings in Paris, a locally-owned coffee shop, offers a flair of European decadence, colorful pastry selection, and speciality coffee drinks that will WOW your morning. Try the Bourbon Caramel latte, if you want to love life.

Dinner reservations should be made ahead of time for either The Hurricane Restaurant or The Boathouse (I had the best shrimp scampi of my life here, and it wasn’t just the fresh Maine air that made it taste better).

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See Maine by train in 4 nights, Kennebunk and Kennebunkport restaurants

See Maine by train in 4 nights, Kennebunk and Kennebunkport restaurants

If you’re not too tired, after-dinner fun can be had at one of these spots.

1. Taste all the beers at Federal Jacks and Kennebunkport Brewing Co.

2. Try the sweet nectar, known as mead, at the Honeymaker Mead Room.


Tip: If you want to make this a 2-night getaway instead of a 4-night vacation, then 1) spend two nights in the Kennebunk area, 2) take the train back to Boston, and 3) fly home. Remember those pick-a-path books? I feel very much like I’m in one right now.

Stop here. Do not go forward. Return to Boston. Then, go home.


Moving on, night two, the second stop.

As we left the Kennebunks to head back to the Wells Train Station and continue our train ride north, we made a pit stop for lunch at a funky restaurant with top-notch cocktails called, The Bitter End. It was here that I discovered the nautical origin of the term “the bitter end,” which refers to the end of a ship’s anchor rope. Did you know that? I must literally be the last person to know that?

Try the Bitter End’s calamari and onion strings and their bitter marg.

See Maine by train in 4 nights, Bitter End, Wells, Maine

See Maine by train in 4 nights, Bitter End, Wells, Maine

Welcome to the “other” Portland.

We arrived in Portland and said farewell to the Amtrak Downeaster (again), but just for the day. We’d be back on the train the following day.

Locals told us that Portland, Maine, is known for having more restaurants per capita than San Francisco. In fact, Portland was deemed Restaurant City of the Year by Bon Appetite.

Well, if that’s the case, where should I eat in Portland?

The Shop - the best and freshest oysters for $1.25

The HighRoller Lobster Co. - surf and turf burger will change your life

Hot Suppa - try them for breakfast

Local 188 - make reservations ahead of time

Becky’s Diner - easy breakfast diner on the harbor

Holy Donut - FAMOUS donuts with unique flavors made from mashed potatoes

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How to get around in Portland, Maine, for FREE.

If you book a hotel with a shuttle, or catch an Uber and stay downtown, then you won't need a car. There are so many beautiful places to stay in Portland, Maine, that I'm not sure I can tell you THE BEST place to stay out of them all.

We stayed at the Holiday Inn. On the hipster scale of hotels, this one was definitely not the coolest, however, it was centrally located and offered a FREE shuttle to guests. We used this shuttle to explore the city, which meant, we didn't have to blow our budget on Ubers, but could use our money for better things, like stuffing our face with lobster rolls and oysters!

Here’s what you MUST DO in Portland.

Because Portland is a waterfront city, it isn’t surprising that 2 of the 3 things I’m about to recommend are on or near the water.

See Maine by train in 4 nights, Portland Head Light

See Maine by train in 4 nights, Portland Head Light

  1. Harbor Cruise

    While there, we took a harbor cruise of Portland, Maine. This Casco Bay cruise is one of the most highly recommended boat tours in Portland. Taking a boat ride in Portland, Maine, is a terrific way to see a variety of picturesque lighthouses, including the most photographed lighthouse: Portland Head Light.

  2. Lobster fishing

    Want to do some real lobster fishing; venture out on a lobster cruise, like Lucky Catch Cruises during Maine’s lobster season. Lobsters are harvested year round, however, the best time for lobster fishing is June through December.

  3. Victoria Mansion

    For the travelers who want to stay dry, you can check out this historical mansion in town.

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How to eat the FRESHEST lobster you’ve ever had.

Take a Lucky Catch Cruise and catch your own lobster. Purchase it from the captain for abrout $5-8/lb., then take your catch to Portland Lobster Co. or Dimillo’s on the Water, both just steps away from the dock. These restaurants will steam your freshly caught lobster for about $12 and throw in some sides! Enjoy!!

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See Maine by train in 4 nights, Portland, Maine Lobster

See Maine by train in 4 nights, Portland, Maine Lobster

Here’s a handy list of Portland, Maine, beaches:

Crescent Beach State Park

Willard Beach

East End Beach

The train departs for the third night’s stay in…

Freeport, Maine, which is known best for its shopping. Freeport boasts a city-wide outlet mall just across the street from the train station.

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See Maine by train in 4 nights, Freeport Outlets

See Maine by train in 4 nights, Freeport Outlets

Freeport is home to one of Maine’s most visited attractions, a store with a giant boot.

The L.L. Bean Flagship Store, with its giant-sized boot out front, is a mecca for travelers. Opened 24-hours a day, L.L Bean is one of the most iconic stores in Freeport, Maine. Be sure to look for and read about the fighting moose in the window.

What else can you do in Freeport, Maine, besides shopping?

Well, you can eat.

Sit out on the patio with a firepit at Linda Bean’s Maine Kitchen or try Kamasouptra in the tiny food court.

Tip: If you go to Kamasouptra, mix their Jalapeno Beer and Cheddar with the Grilled Cheese and Tomato soup for a cheesy soup delight. This combo was recommended to me by a local! Thank God for locals’ recommendations.

Off for the final night’s adventure, and it’s a “boozy.”

Board the train in Freeport and head north for the final night’s stay in Brunswick, Maine. You’ll need a car here to explore the surrounding villages. Enterprise rental company is 1 mile from the train station.

From the train, cross the street to the Brunswick Hotel and Tavern.

This is where you’ll stay for the night. Brunswick, Maine, offers a few lodging options, but none as convenient to the train traveler as the Brunswick Hotel and Tavern. Just across the street from the train station, the hotel also has a full-service restaurant in the lobby.

Vessel and Vine, cocktail class, Photo cred: Maine’s MidCoast

Vessel and Vine, cocktail class, Photo cred: Maine’s MidCoast

Cram your day in Brunswick with as many of these sites as possible.

  1. Harpswell - the oldest town in Maine, take a stroll to see the Giant Stairs.

  2. Vessel and Vine - take a cocktail class at this locally-owned speakeasy in the basement of a church. This was one of the highlights of our Brunswick trip—experimenting with booze in a vintage setting over fine plates of cheeses and olives was all kinds of wonderful.

  3. Bowdoin College - stroll through the campus and take photos of the beautiful architecture.

  4. Bath - a quintessential Maine village on the Kennebec River, this town’s center is straight out of a movie scene. Be sure to eat at Bath Brewing Company and try a flight of their beer.

  5. Maine Maritime Museum - love historical sights and/or boats? Then, you’ll love this museum, America’s only surviving shipyard site where giant schooners were built.

  6. Red’s Eats - a popular food stand featured on various food networks, known for their lobster rolls. Locals tend to think this spot is overrated. Instead, we had a whole lobster at Cameron’s Lobster House, an old-fashioned diner with no wait and great service.

  7. Popham Beach State Park - Maine’s busiest state park beach

Wherever you go, be sure to grab a paper map from the train station before you explore Brunswick and its surrounding areas.

Cell service is sketchy around these parts. It will be handy to have an overview of which direction you should be heading in, in case you lose signal.

That’s it.

In just 4 nights, you will have journeyed up the coast of Maine. Let me know if you end up taking the trip. I’d love to hear your experience!

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