Boston & Maine: Eastern Line

This bike trip pays homage to the Eastern Railroad, which ferried passengers between Boston and Portland throughout the 19th century. Go in peak summer, because this trip is best enjoyed hot and sunny. In Maine, that generally means mid- to late-August into early September. 

This bike trip also features more on-road riding than I generally prescribe. All of Day 3 and about half of Day 4 run for the most part along coastal roads. The good news is that drivers in this part of the world tend to be bike friendly. Unlike their New York brethren, most Massholes will wait patiently—and quietly!—behind a cyclist for a safe opportunity to pass. Vacationland makes everyone nicer.

Day 1: Boston >> Salem

Start with a little pizza. North Station is conveniently located a stone’s throw by bike from Regina Pizzeria. If pizza isn’t your pre-ride jam, there are no shortage of other eateries close by.

And then continue with a little history. Leaving North Station you’ll pass through Charlestown, which is the oldest neighborhood in Boston. Take a few to visit Paul Revere’s Ride, Boston National Historic Park (home to the USS Constitution), and Bunker Hill. They make for some nice sights to get you through the not particularly appealing suburbs that follow on the north side of the Mystic River. They also make good spots for bike selfies.   

Take a detour to Nahant. It’s a completely unnecessary detour, but oh so worthwhile. Nahant is a strikingly beautiful spit of land that has no business being a peninsula. It’s effectively an island you can bike to, thanks to the sand-flanked causeway that connects it to the mainland, otherwise known as Nahant Beach. Do a loop of the island (watch out, it’s hilly!) and be sure to see Lodge Park, East Point Loop Station, Forty Steps, and Canoe Beach. 

Hit the beach! And you’ll pass plenty of them! Nearly two dozen beaches line the shores between the southern tip of Nahant and Marblehead. In addition to Nahant Beach, you’ll find King’s Beach, Preston Beach, and Devereux Beach, just to name a few of the bigger ones. Personally, I was a fan of Fort Beach in Marblehead, because it’s more of a swimming cove than a big sandy touristed beach.       

See the Salem witches. More specifically, see the Salem Witch Trials Memorial. It’s a sobering tribute to a period of historical insanity. There’s plenty of other less serious witch kitsch in town, if that’s your thing. For maritime history buffs, don’t miss the Salem Maritime National Historic Site.

Eat at Clam Shack. I recommend the lobster roll. Watch out for the seagulls. They’re like Washington Square Park squirrels with wings. You’ve been warned.

Camp at Winter Island Park. For what will appear in photos as an abandoned Coast Guard air station overrun by RVs is actually a surprisingly cool campground and park. Waikiki Beach is a delightful swimming hole and place to watch sunrises. The park bench next to the harbormaster is an equally lovely vista for sunsets.

Day 2: Salem >> Salisbury

Get breakfast in Salem. There’s plenty of sit-down places, and I’m sure they’re great. I was in more of a hurry and opted for takeout from Life Alive Organic Cafe and the neighboring Caramel French Patisserie. They were both tasty.

Trail PSA. The Border to Boston Trail plans to run 70 miles on asphalt or crushed stone from North Station to the New Hampshire border just north of Salisbury, eventually comprising the entire route of Day 1 and Day 2 of this bike trip. As I’ve found with many ambitious trail projects, they tend to have more ambition than well-maintained trail—and this one is no exception.

Things start smooth enough from Peabody to Boxford on the only officially marked section of the Border to Boston Trail. The segment that follows, aka the Boxford Rail Trail, gets bouncier. The final section through Martin H. Burns Wildlife Management Area Trail is rougher yet, running down a dusty service road for the power lines overhead.

Words to the wise: 1) carry snacks and plenty of water, as this is the only part of this bike trip where you’re mostly off the beaten path; and 2) carry spare bike tubes and a pump, as this is the only place I got a flat in all of 2020. According to the official map there is a marked on-road route that bypasses all of the bumps. But where’s the adventure in that…

Eat in Newburyport. You’re likely to come plowing out of the trail dusty, thirsty, hot, and hungry. Conveniently, the trail deposits you directly in front of Metzy’s Cantina at Newburyport Station. For more traditional seafood—or really any other—fare, continue on another mile or so into downtown. 

Camp at Salisbury Beach Campground. Take a dip while you’re there. For more shade and (maybe) fewer RVs, consider nearby Pines Camping Area instead.

Day 3: Salisbury >> Wells

Get an early start! There are a lot of stops along the route today. You’ll want the time to enjoy them. 

Get breakfast in Salisbury. I can’t personally vouch for either, but the Googlerati recommend GroundSwell Surf Café and Vinnie's Beachside Café. 

Riding Route 1A. You’ll spend much of the day on this road that hugs its way up the coast. Don’t let the first few miles dispirit you. I know, it looks like New Jersey-by-the-sea. I promise, it gets better. Once you clear Hampton Beach, the views get nicer as the road winds its way along the craggy coast flanked by old world mansions. You’ll also pass several state park beaches between here and Portsmouth, including North Hampton State Park, Jenness State Beach, and Wallis Sands State Beach. Take a dip! 

Take a (quick) break in Rye. Grab a bite at Rye Harbor Lobster (I recommend the lobster roll), check out Rye Harbor State Park, and take a bike selfie at the 1614 Monument. Take another quickie to saunter through Odiorne Point State Park. 

Slow roll through Portsmouth. Portsmouth is a gem of a city. Start with a stop at the Wentworth-Coolidge Mansion. Grab another bite at Geno's Chowder & Sandwich Shop. I vote chowder here, because there are more lobster rolls to come. Make your way along Strawberry Banke and up to Market Square. Go to a personal favorite, the Portsmouth Book and Bar, or take your libations without literature at the Portsmouth Brewery. Roam around a bit before crossing over the Memorial Bridge into Maine.

Welcome to Vacationland. The route from here on out is chock-a-block full of sights and stops. Enjoy! 

• In Kittery take in the view at Fort McClary State Historic Site. Just up the road and across the street, head down to Barters Creek (entrance not marked on Google Maps) for a dip in my favorite swimming hole. If you’re as scared of sharks as I am, you’ll appreciate that the only connection between this body of water and the ocean is a drainage pipe that is too narrow for Jaws. Everybody else will appreciate that this shallow creek runs about 10 degrees warmer than anywhere else you’ll get wet around here. Grab eats at Chauncey Creek Lobster Pier. I recommend the lobster roll, obviously. Down the road check out Seapoint Beach, a hidden gem that is next to impossible to get to on anything other than a bike because parking is overwhelmingly for residents only.
• Continue up Route 103 to York and wave at my in-laws along the way. Stroll across the Wiggly Bridge, then turn around and meander down Fisherman’s Walk to York Harbor Beach. Emphasis on the “walk”, do not ride your bike on this path! Hop back on the saddle and continue down Route 1A along Long Sands Beach and up to the Nubble Lighthouse. Great spot for a bike selfie (see the lead photo for this trip above). Follow the curve of the peninsula down to Short Sands Beach and stop at The Goldenrod for old school salt water taffy or the York Beach Beer Company for more adult fare. Get your lobster roll fix at Shore Road Market and continue up, you guessed it, Shore Road.  
• In Ogunquit check out Perkins Cove Drawbridge for an impossibly quaint harbor view. Enjoy an overpriced lobster roll at Lobster Shack. Meander along Marginal Way and down to Ogunquit Beach. If the tide is out, the sand is firm, and your tires are wide enough, I recommend biking the beach from Ogunquit to Wells. If that doesn’t work, hop onto Route 1 and ride the remaining few miles into Wells.

Camp at Wells Beach Resort Campground. Treat yourself to a cone from Scoop Deck and a round of mini golf to mark the end of a jam packed day!

Day 4: Wells >> Portland

Start your day at Congdon’s Doughnuts. Did you know Dunkin’ Donuts is a New England creation, Massachusetts specifically? I didn’t either, nor did I appreciate the deep, deep love for “Dunkies” in this part of the world until I married a Mainer. All this is to say, start your day with a doughnut. In my view, Congdon’s is a world better than any Dunkies. Judging by the lines at this local favorite, it’s a view that is widely shared. Get there early.

Second breakfast at Boulangerie. A short way up Route 1 in Kennebunk is a delightful little French cafe with tasty pastries and great coffee. You can only eat so many doughnuts, after all.   

Enjoy Eastern Trail. No doubt this well-maintained trail will come as a welcome relief after a day and half on roads. Following the old right of way of the Eastern Railroad, the trail is a straight shot to Scarborough. Make a lunch stop at the Palace Diner in Biddeford, which is just about halfway. My wife swears by the place.

Grand finale in Cape Elizabeth. The last 25 miles of this trip are a real joy, compliments of the astounding natural beauty of Cape Elizabeth. Follow Routes 207 then 77 southeast to Kettle Cove. Take a break, take it all in, go for a swim. Ride a mile down the road to Two Lights State Park. You may have to pay a small entry fee—it’s worth it. Next door is The Lobster Shack at Two Lights. It’s overpriced and you’ll almost certainly wait in a long line, but it’s such a beautifully epic place to eat a lobster roll that it’s worth it as well. Heading north toward Portland you’ll next hit Fort Williams Park, home to Portland Head Light, the mother of all Maine lighthouses. It’s a hell of a grand finale. Take a bike selfie. Wrap it all in a bow with stops at Willard Beach and Bug Light Park, before crossing the bridge into Portland proper.

Spend a night (or two) in Portland. Having biked some 180 miles over four days it would be a shame to just head straight to the train station. Stay a while, Portland’s a cool town. Assuming you’ve had your fill of lobster rolls, eat at Bao Bao, a dumpling house run by one of the country’s premier Chinese chefs. Cong Tu Bot for Vietnamese and Duckfat for fries and other Euro-fare are also good options. Tandem Coffee and Bakery makes great coffee and an extraordinary breakfast sandwich. Spend money on unnecessarily expensive (and fashionable) sundries at Portland Trading Co and Portland Dry Goods. Visit Victoria Mansion. Bike the Eastern Promenade Trail and the Back Cove Trail. And if you’ve really got time to kill, hop Casco Bay Lines to any number of the islands that dot the bay.

Trails

• Northern Strand Community Trail
• Marblehead Rail Trail
• Independence Greenway
• Border to Boston Trail
• Boxford Rail Trail
• Martin H. Burns Wildlife Management Area Trail
• Clipper City Rail Trail & Harborwalk
• Old Eastern Marsh Trail
• Eastern Trail