A Northeast Road & Food Trip Guide: Boston, MA to Portland, ME

Food & Entertainment

Yet another article in which I must confront a pain point in my personality.

You know what? FINE. Whatever’s cheaper than therapy. (Literally everything. Literally, everything is cheaper than therapy.)

When traveling, I’m a bit nuts about where I dine out. ‘Psychopath’ feels like a completely just and fit description.

I don’t mean to be a control freak (of course I do), it’s just, I *hate* wasting my money on shitty food. I hate wasting my time on shitty food. I hate wasting my *tastebuds* on shitty food. I also hate sounding like a pretentious asshole but I understand that I’m failing miserably with that at the moment.

To me, travel IS food, and I geeeeeek out on researching restaurants, combing menus, and stalking local food critics’ twitter accounts weeks in advance to find the best of the best. As fate would have it I’m dating an absolute angel who lets me just do my thing and keeps commentary as minimal as “Where we eatin?” (The only time he’s come close to murdering me — he literally told me once he almost killed me — is when he’s starving and we get hit with the 45-minute wait thing, Which I get, okay?)

The angel and I decided to turn a wedding in Maine into a mini East Coast road trip. I was like, “Perfect, a Monday to Saturday, that is at LEAST 12 lobster rolls I can house before I hit the Portland airport.” I was being very “Bitch Don’t Kill My Vibe” about this lobster roll plan I had. Spoiler alert: the East Coast is packed with some delicious-ass food and while yes, lobster rolls are essential to the list of musts, I was pleasantly surprised by the other delicious fare decorating New England.

So trust me, you’re going to want to save this if you ever do the Boston to Portland, ME thing (which actually only takes like 2 hours because you can drive the length of Massachusetts in 43 seconds.) I went ahead and did all the research for you and trust me, it was my pleasure.

TIGER MAMA (Boston, MA): The Asian Fusion restaurant of all Asian Fusion restaurants. The coolest vibe, incredibly innovative cocktails (it felt like the kind of night to splurge on something that came in a pineapple), and the Pig Rice (A FRIED RICE CONCOCTION WITH BACON. WITH. BACON)? I could not possibly speak highly enough about it. And because this is important to me: perfectly-temped still water.

ISLAND CREEK OYSTER BAR (Boston, MA): We popped in here to get a quick Tour de Massachusetts of oysters and a glass of rosé because we’re suckers for a nice bar to post up at. Consensus? We couldn’t have nailed a better date night spot if we tried. My boyfriend would also like me to tell you that they have some fancy beer system that keeps all of their tap beer at the perfect temperature.

THE HAWTHORNE (Boston, MA): Because I’m a “Just one more!” kinda gal, we popped into the Hawthorne for a quick nightcap, and duuuuuuuuuude: THE. COCKTAILS. Stick with the menu or have the bartenders just wing it. We went with the latter and ended up with the most insanely hit-the-spot-good gin cocktail that I would describe best as an inside-out Old Fashioned? Also, the bar has a “friend’s rich basement” vibe, which works for it.

TATTE BAKERY (Boston, MA): Ah yes, onto the Instagrammable coffee shop. Tatte Bakery has a whole lot more going for it than its aesthetic; their pastries are “ARE-YOU-FUCKING-TASTING-THIS?”-good. The coffee’s also great but I was secretly jealous of my boyfriend’s mint lemonade.

NEPTUNE OYSTER (Boston, MA): I was prepared to wait my ass in line two hours if I had to for the legendary Neptune Oyster lobster roll. I found the secret: pop in for a weekday lunch. The wait was only a half hour, they take your number and call you when they’re ready, and you can walk right on down to Mike’s Pastry (an OG Italian pastry shop) to grab a cannoli for your post-butter-dripped lobster sandwich dessert. Did I mention calories don’t count on vacation? P.S. Sleeper hit at Neptune: the clam chowder.

ROW 34 (Boston, MA): I went to Row 34 with the sole mission of destroying multiple dozen-oyster platters and I’m incredibly pleased to report back that I did just that. This place is kinda crowded and the bar is the best (there’s a waitlist for that too) so throw your name down and hold tight. While I’m usually a wine-with-oysters kinda gal, a fellow bar-mate let us know they have the best beer list in the city, so I’m passing along the insight. Still not full after oysters? (Me neither duh) Get the crab toast.

CLAM BOX (Ipswich, MA): OH MY GOD, this lil bb road-side shack, I cannot. My advice: starve yourself that morning. You’ll want to claw your eyes out by the time you get to this little highway gem but it will be so worth it. It’s strategy; I cannot advise you on which menu item to order because it’s all incredible so for $29 get the fisherman’s platter and try everything. All of the fried seafood. All of ’em. Also – homemade tartar saaaaaauce.

Roy Moore Lobster Co. (Rockport, MA): Rockport is half “touristy town filled with seventy ice cream shops and boutiques your old aunt likes to buy pointless shit at” and half romantic seaside village where you imagine authors hole up to write their novels. Roy Moore Lobster is the hidden gem. For $40 you can get three pounds of lobster and enjoy the salty air on their back deck while melted butter drips down to your elbows.

Anju Noodle Bar (Kittery, ME): I will talk about this place until I die. Here I go with that whole pretentious asshole thing again but, ever since I got back from Tokyo last fall, it’s been really, really hard to find ramen that measures up. Miiiiight have something to do with the fact that their broth is made using bones from the butcher shop next door. It’s perfection. I’d be remiss not to mention the staff as well; I left feeling like I had new friends.

Palace Diner (Biddeford, ME): Here it is! The place we waited in line for 45 minutes and Erik almost killed me! Memories. Palace Diner is a charming-as-heck 15-spot train car where you will probably have to linger outside an hour beforehand, but you’ll be kindly rewarded with the world’s best breakfast potatoes. Try not to make eye contact with people while you lick your plate after you finish the Deluxe Sandwich, it’ll be all weird.

The Well at Jordan Farms (Cape Elizabeth, ME): Yes, I absolutely died upon the sight of this place, thank you SO much for asking. I mean, there’s farm-to-table, and then there’s your-table-is-literally-on-the-farm. You’ll want to get to your reservation early so you can walk around this 122-acre third generation farm and marvel at how people actually do this for a living. Oh and I can’t even talk to you about the donuts they have on the dessert menu or I’ll pass out.

Tandem Coffee (Portland, ME): I’ve always been a sucker for a well-branded hipster coffee shop and folks, I probably always will be. We got here at like 8:30 a.m. on a Saturday and the place was already poppin’ so plan accordingly. Easily my favorite coffee of the trip (MEDIUM ROASTS FOR LIFE) and they had a cinnamon roll that had little whispers of orange zest. Life was beautiful in that moment.

Holy Donut (Portland, ME): I never knew how much I needed mashed potatoes in a donut. If you’re grossed out by this it’s because you’re thinking of like, garlic and chive mashed potatoes. No. Wrong. Back Up. Just straight up potato, mixed into a donut, purely for texture reasons, and honestly? Mashed potato-infused donuts for fucking president.

Eventide Oyster (Portland, ME): BROWN. BUTTER. LOBSTER. ROLL. BROWN. BUTTER. LOBSTER. ROLL. We ordered that thing and the waitress wisely accommodated, “I’ll split it in half. Not doing so has caused breakups.” Yeah wow, I would’ve stiff-armed him for the last bite. We thought about ordering one or six more but opted to try more of the menu. UMM. Glad we did. The oysters come with flavor-infused ice to put on top which allows the horseradish, pickled red onion, or whichever you choose to infuse itself all over that little bi-valve.

Ugh. Reliving all of this has me wiping drool off these keys (I’ve been shoving my face with pita chips and hummus trying to stave off this faux-hunger I’m feeling writing this). In the words of Arnold Schwarzenegger: I’ll be back.

Oh, and one more word of advice? When you get to the Portland airport, stick with McDonald’s. Just… trust me.

Image sources: 1 / 2 / 3 / 4 / 5 / 6 / 7 / 8 / 9 / 10 / 11 / 12 / 13

Liz Welle is a professional feelings feeler but gets paid to do social and digital stuff for brands in Minneapolis while occasionally food styling on the side. She lives in Uptown with her boyfriend and their thirteen plants. She is doing her best.








BY Liz Welle - September 23, 2017

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add a comment

  1. Charmaine Ng | Architecture & Lifestyle Blog

    September 23rd, 2017 at 10:56 am

    I appreciate this guide so much. I’m the EXACT SAME AS YOU. I need to plan everything down, especially where I eat. I mean, I need to save quota for only the best food! Every photo on this post makes me drool!

    Charmaine Ng | Architecture & Lifestyle Blog

  2. Liz Welle

    September 23rd, 2017 at 2:49 pm

    Finally someone gets me!! <3

  3. Krystal

    September 23rd, 2017 at 1:11 pm

    We visited Boston over the July 4th weekend but stayed in town. We couldn’t get into Neptune (“The wait right now is six hours”) but went to newcomer North Square for a mind-blowing lobster roll. That Boston to Portland drive is definitely bucket-list for me (well, as in like, before-I’m-30 bucket-list)!

  4. Liz Welle

    September 23rd, 2017 at 2:50 pm

    You HAVE to do it it’s incredible. We kept saying too how I’m sure the fall is just crazy beautiful there.

  5. Allegra Ghiloni Fashion Stylist

    September 25th, 2017 at 4:18 am

    This looks absolutely amazing! I will definitely be adding this trip to my bucket list! Thanks for sharing!

    Allegra xx

    Allegra Ghiloni Fashion Stylist

  6. Chesley

    September 25th, 2017 at 6:09 am

    I love this! I always try to plan ahead, but end up anxiously yelping for the best places as I get hungry in a city. Usually it works out, but a little planning up front clearly goes a long way. Also, your narrative style is really refreshing and fun!


  7. leslie

    September 25th, 2017 at 11:28 am

    I’m literally the same way! I will book a place to stay and then it’s all about where we will eat. everything else is secondary haha


  8. Stacy

    September 25th, 2017 at 6:08 pm

    I had to stop about a minute into this post to eat a leftover slice of bread that came with my salad at lunch today because these descriptions made me absolutely ravenous. I’ve been to the east coast before, and wanted to go back but now I have about a dozen more reasons to return. Everything here sounds incredible, and I’ve never wanted a lobster roll more in my life (and I crave them often.)

  9. Liz Welle

    September 26th, 2017 at 9:55 am

    LOLOLOLOL! Thank you for this comment it made my day.

  10. Lam Rou

    September 25th, 2017 at 9:21 pm

    This post is literally my life & it’s great to know people understand this food is life mentality I have in my city & especially on vacation. I wish I seen this this when I was in Maine & Boston. I wasn’t a fan of the brown butter lobster roll a Eventide but their sablefish was pretty good. I’ll be back to read more of your recommendations.

  11. Liz Welle

    September 26th, 2017 at 9:54 am


  12. Kate @ Cooking On Clocks

    September 26th, 2017 at 9:47 am

    What hotel did you guys stay at in Boston? Looking for recommendations!

  13. Liz Welle

    September 26th, 2017 at 9:54 am

    We actually stayed in an Airbnb in South End! Highly recommend!

  14. Rachel

    September 27th, 2017 at 1:15 pm

    You get me. Thank you for doing my Boston research for me. Ever so grateful to know there’s another gal out there driving her partner bonkers about wait times for a meal. There’s an app that you might be interested in called Snatch. It is so helpful for keeping track of all your research. The name is an added bonus when someone asks for a restaurant recommendation and you get to say, “Oh, hang on, lemme just check my snatch!”

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