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Despite being a native New Englander, it took 30 years for me to make it to Portland, Maine! That shouldnt have happened! ‘t was high on my list of places to see – it’s a very foodie-oriented city, on so many “up and coming” lists, and only two hours from Boston.
Then I finally got an opportunity – my dear friend Lisa’s bachelorette party.
Lisa gave us largely free reign on planning her bachelorette (brave woman!). She wanted something more low-key and not too crazy, maybe with some wine-tasting and cocktails, focused more on friendship and bonding than partying. At first, we had been planning to do the party in Boston — it’s 20 minutes from our hometown. But I wasn’t quite sold.
I used to be a Boston nightlife writer and was a fixture on the club scene until my mid-twenties. Staying out until 4 and then going to work the next day was a weekly habit (yes, I’m aware that Boston’s bars close at 2; you’d be surprised what you can find after they close!). I preferred the high-end nightlife and hated places like Faneuil Hall, where I couldn’t go out without running into people from high school.
On the same wavelength, I did not like Boston’s bachelorette parties. I hated going out to one of the nicer clubs and being surrounded by girls in sashes doing tequila shots, slobbering over random guys, and throwing up in the bathroom. It made even the nicest clubs feel like amateur hour. I don’t like doing amateur hour in my home city.
Plus, all of my favorite places have closed in the 4.5 years since I moved away (R.I.P. Saint, The Otherside Café, 28 Degrees, TC’s Lounge).
Then an idea popped into my head.
“Why don’t we do Portland instead?” I asked my fellow bridesmaids. It would be fun and different and would guarantee a level of anonymity we wouldn’t have in Boston. Plus, the parents of one of the bridesmaids own a house in Maine, not too far from the city. We could probably crash there with no worries.
A bit of research later and we realized that Portland was the perfect choice for Lisa’s bachelorette party. Here are the highlights of our trip.
Drive Up: New Hampshire State Liquor Outlet
I’m not sure I should definitively list the New Hampshire State Liquor Outlet as a highlight, per se, but hey — if you’re driving from Massachusetts to New Hampshire and looking for booze for the hotel, this is as cheap as it gets. No taxes. Live free or die, baby!
Tasting #1: Maine Craft Distilling
Pulling into town with some time to go before our lunch was ready, Beth suggested we stop at Maine Craft Distilling. It couldn’t be a better place to get to know Portland — we started our day tasting unusual varieties of spirits, including blueberry moonshine and Queequeg rum.
Maine Craft Distilling is unusual, quirky, and a lot of fun, just like Portland itself. The space is beautiful, too. You can taste for free here!
Meal #1: Duckfat
Duckfat is one of the hottest restaurants in Portland – and it’s a sandwich place! They’re famous for high-end sandwiches and French fries, which are cooked in duck fat, naturally.
Duckfat doesn’t take reservations and there was a 2.5-hour wait when we called – for LUNCH! At a SANDWICH PLACE! So we decided to order takeout sandwiches and fries instead, which was probably the smartest thing we did all weekend, as our order was ready in just 20 minutes and we could take it to the hotel.
I went for the duck confit sandwich and fries. Outstanding, no surprise! Make sure you pick up some truffled ketchup as well.
Tasting #2: Maine Mead Works
Have you ever tasted mead before? It’s becoming more and more popular (I’m convinced Game of Thrones’s popularity is a factor). We booked a short tour and tasting at Maine Mead Works.
Mead is similar to wine, but there are big differences — it’s made from honey and is very sweet, which can be tough to get used to at first, but after several different tastes (I loved the ginger mead in particular!), I was a big fan.
Tastings and tours are available from $5. Check out the schedule here.
Walk-By: Bunker Brewing Company
If you’re walking from Maine Mead Works to Urban Farm Fermentory, you’ll walk right past the Bunker Brewing Company. None of us were really in the mood for beer tasting, so we just stopped in long enough to check it out.
The building, a “1920s era garage of a defunct Portland scrapyard,” reminded me of the random abandoned-looking buildings you see in Melbourne that hide chic cafes and restaurants.
Tasting #3: Urban Farm Fermentory [closed in 2024]
Our next stop took us kombucha and cider tasting! Seriously. Urban Farm Fermentory hosts several varieties of both kombucha and cider on tap. You can get a paddle of four samples for just $3.
Beth and I split two paddles to taste as many as possible. Ginger kombucha and strawberry kombucha were highlights, and all of the ciders were excellent.
Tasting #4: Sweetgrass Farm Winery and Distillery
Because we HAD to taste wine at some point! Sweetgrass Farm Winery and Distillery is on Fore Street, in the heart of downtown Portland. While wine is on the menu, I found the spirits to be the highlight, especially the Back River Gin, cranberry bitters, and cranberry splash wine.
You can taste four wines or spirits for $5. Definitely worth a visit.
Meal #2: Congress Squared
Being a major foodie city, we were spoiled for choice of Portland restaurants. But with the five of us with widely varying food preferences and dietary restrictions, we needed to find a place that worked for all of us. We chose Congress Squared in the Westin hotel.
Hardly anyone was dining at the restaurant that night — I was surprised, because the food was delicious! Big props to the chowder and the roasted duck breast.
Nightlife: Wharf Street Clubs
We hung out at the Westin for a bit, checking out the cocktail bar upstairs and debating whether to crash the wedding downstairs (our verdict: too small! We settled for congratulating the mother of the groom in the ladies’ room, in between taking ladies’ room selfies). In short, it was time to grab an Uber and head to Wharf Street, home to the center of Portland’s nightlife.
I found the Wharf Street club scene to be very Faneuil Hall – very young, cheap, and basic. And everything shut down by 1:00 AM. Not my scene, but sometimes it’s fun to just let loose and go crazy while surrounded by 22-year-olds in an unfamiliar city.
Most of my readers recommended the nightclubs Pearl Lounge and Oasis. We tried out both, but spent the most time at 51 Wharf. All three are located on and around Wharf Street. Thanks to no cover charges, we were free to go back and forth all night.
No photos from the later hours of that night, because what happens at a bachelorette party is best kept under wraps!
Our Digs: Residence Inn Portland
Turns out we didn’t need to crash outside town after all – Beth’s father generously booked the five of us a suite at the Residence Inn. (Thank you, Don!)
Our suite included a bedroom with a king-sized bed, a bathroom with a full-sized tub, and a living room/dining room/kitchenette with a pull-out queen-sized sofa. We also brought an air mattress so all five of us could fit.
The Residence Inn is in a good location – you can walk to most interesting destinations in Portland within 20 minutes and they have a free shuttle you can arrange. If not, Uber is easy and surprisingly cheap (compared to Boston and New York!) for getting around in Portland.
The Morning After
Woke up to a text from my dad: “R u home or still incarcerated?” My dad knows my friends well. He wasn’t that off base.
Then I found a handwritten note from the bride: “Guys, Lisa is downstairs getting coffee (not missing like The Hangover).”
At that point I could not stop laughing!
Meal #3: The Maine Diner
The Maine Diner, located south of Portland in the town of Wells, is one of my favorite restaurants in the world. I’ve written about it here and go every time I’m home. Lisa is actually the one who introduced me to it (her brother Paul is probably more obsessed than the rest of us put together!).
Their seafood chowder is legendary. Seriously. This New Englander has never had a better chowder anywhere in the world. You WILL get huge chunks of lobster and scallops in it, along with fish, potatoes, clams, and more.
I usually go for the Jim Nantz – a cup of seafood chowder (sometimes I’ll upgrade to a bowl!) served with a hot lobster roll with melted butter. Perfect for lobster lovers who hate mayo like I do!
The Takeaway
Portland is so much fun! I’m so glad we chose it for Lisa’s bachelorette party. If you’re in the New England area and looking for a bachelor or bachelorette destination, or even just a fun weekend away, I encourage you to consider it! Bring your appetite.
An overnight was fun, but I’d recommend going for a whole weekend if you can swing it. I’ve got a big list of things to do on my next visit — many of them from this foodie post from The Travel Bite. And New England with Love has a post about beaches in Maine that would be great for next time!
The most important thing is that the bride had a blast. As she gets married a week from tomorrow, she’ll know we sent her off in style!
Essential Info: Most of the tastings are easy enough to walk into and charge less than $5 for a tasting. We booked Maine Mead Works in advance so we could have a tour as well; for the rest, we just walked in.
Studio rooms at the Residence Inn Portland start at $152. Two-room suites like ours start at $163. See more accommodation options here.
Want to explore more of Maine? See our guide to the artsy town of Ogunquit, Maine and the fun things to do in York, Maine.
I am BEYOND impressed and even delighted by this post. New England (particularly Rhode Island) is my second American home, after New York. As a born and raised Moscuvite and big-city girl I could not WAIT to get out of there (when I moved to the US, I spent a few months in Maryland before moving to RI – before high-tailing out of there to college in DC and then NYC after graduation). So, New England for me has always been such a backwater place, although I know it is mostly the result of my own prejudices and lifestyle preferences than the reality. Whenever I visit my dad in RI, it always feels like temporary exile.
So it’s really fantastic to read about all the interesting activities and amazing foods one can find in the area. It kind of relieves my anxiety – I know where to get away to for a bit of fun and sophistication, if need be.
Ha, as a native New Englander, it doesn’t feel like a backwater to me at all! Especially in the cities.
I’m so glad you loved Portland. That’s my home! I’m quite fond of it and we do have some really really good food and drinks. I think its funny because I can’t stand Pearl or Oasis because they’re always full of people I went to high school and just annoy me to death. Hopefully you guys didn’t wipe out on the cobblestones of wharf street- they’ve been known to take down a girl or two 🙂
Hahaha. Yet another similarity to Faneuil Hall — you see girls hobbling all over the place in their stilettos!
I’m a big fan of you covering cool areas in America! Always my favorite posts in the location-specific category. While it’s great to read about your travels in other countries, it’s much more of a reach for me to get there. There’s so much to mine in American travels, right in our backyards, and I would love to see you cover more!
My road trip through the American South last year was one of my favorite trips ever. There’s so much to see here!
Looks like you girls had a lot of fun. Portland is on my list of cities to visit. This post just makes me want to visit now.
BTW, where did you buy your sunglasses or who makes them? I love them!
Thank you! They are the Lafayette sunglasses by Elizabeth and James. The Olsen twins’ line. 😉 Trust me, it’s a GREAT fashion line!
Now this is what I call hanging out with girlfriends, even if it is a hen night type of thing. Good food and a variety of quality drinks, at interesting place. In Portland of all places. Yeah, sign me in!
Very nice. 🙂
I’ve never been but it definitely looks like my type of city!
Can’t get over the queue time for a sandwich place! x
This is a nice post. I love to see the lovely girls here. I definitely like to travel there. This is a lovely place where I can stay few times with my girlfriend. She will be happy to visit this dazzling place with me. Thanks for this crazy post!
Sending this to my sister so that she cancels the pole dance lessons for my bachelorette and makes my tummy happy instead! Portland looks like a lot of fun and a cool destination for a bachelorette party!
Pole dancing is such a cliche — Portland is not!
Looks like you girls had a lot of fun. Portland is on my list of cities to visit. This post just makes me want to visit now.
BTW, where did you buy your sunglasses or who makes them? I love them!
Thank you so much! They are the Lafayette sunglasses by Elizabeth and James (yes, the fashion line by the Olsen twins — it’s probably the best celebrity-run label out there).
I love your posts about America!
And I’ve got to say that your day and evening sounds a lot better (and classier) than the usual bachelorette parties you hear about!
What can I say….we’re pure class. (Inserts photo of us rolling around in a gutter in Vegas.)
Ahem …. SHIPYARD BREWERY!! Because they only make THE best pumpkin beer on the market! And the tasting session in the brewery that follows the “tour” is a great chance to try everything else they make and sort out which ones you like. You guys need to go back. 🙂
Oh, I love pumpkin beer, and Shipyard is right next to the hotel where we stayed! Must return!
I’ve only been to Portland once but I loved it and it has been on my “go back to” list for awhile. One of my daughter’s good friend lives there and she has been to visit her a few times lately. She has been telling me all kinds of fun they’ve been having there. Gonna have to get back sooner than later! Looks like a very fun bachelorette weekend!
I love Portland, Maine! I also went for a wedding and tried so much AMAZING FOOD. Duck Fat was our favorite, we loved the milkshakes! I popped my oyster cherry at Eventide Oyster Co. and tried sweet potato donuts at Holy Donut. All in all-best foodie spot ever. I’m so happy you had a great time!
If you love oysters, one of my favorite places in the world is Neptune Oyster in the North End of Boston. TINY place, get there early!
Definitely sounds like my kinda place! We didn’t have much time on our New England road trip so we only passed through Portland – big mistake. I was watching ‘Treehouse Masters’ a couple of days ago and they were in Portland making a treehouse for the owners of Duckfat funnily enough – it turned out AMAZING. I will have to send the link to this to my best friend and man of honour who will be organising my hen’s party, craft alcohol tasting and lots of delicious food sounds like the perfect idea 🙂
That’s great! I love that this inspired you to plan the same kind of party!
Looks like you had a fantastic time! I want to also be more of a fixture on the club scene, back home in New Zealand it is really dead with only a few clubs catering mainly to 18-23 year olds.. It would be great to find a city with more variety.
That lobster roll kills my life! It looks so amazing! We have nothing like that here in Brisbane so I’m glad I can salivate via your post!
If there’s any reason to come to New England, that is it!
Great to see that Portland East has almost as many tricks up its sleeve as its western cousin in Oregon … great post!
Ah Katie, you were in my backyard! Well my backyard once upon a time. Originally from Maine, rerouted to Nashua and now traveling… well wherever my love and I can.
From your post it looks almost like you did the Maine Brew Bus Tour! We went back to Portland (where it all began for Bill and I) last year on our one year anniversary for the weekend and we did the Bus Tour. Needless to say, by the time we got off the bus we were very good friends with EVERYONE on the bus.
Much like you, we enjoyed the microbreweries and the food. Adding our one year anniversary to relive our time there… well it’s a must for anyone traveling New England!
Enjoyed your post!
I’ve only been to Portland once, for only a few hours, but I liked what I saw. I hope to return someday and see more of it. I’d definitely like to try the various tastings, so I greatly appreciate your reviews of the different establishments. Thanks!
p.s. Congrats to the bride!
Portland is so charming! And what a great idea for a bachelorette. I’ve been planning all of mine for the friends’ weddings I’m in in Charleston, Savannah, NOLA or Nashville. Maybe I need a change of scenery…
You should!! It’s definitely offbeat but good fun.
Fun photos, and excellent article. My SO and I will be visiting Portland in Maine. Looks like the weekend away we need. Is there a hotels within walking distance of the bars that you would recommend? This article mentions 4 hotels that are well received and in our budget, Portland Regency, Portland Harbor Hotel, Embassy Suites, Hilton Garden Inn, https://www.hotelsnearme.co/content/what-are-best-hotels-while-visiting-portland-maine But I am looking for something close to the hot spots. Thank you advance for your advice.
I can only speak to the one hotel that I stayed in because I did not stay in any others. 😉 Many of those are chains — go with a chain that you’re comfortable with!
Hey Kate!
Portland, ME is about an hour from where I live so I head over there frequently!
You packed your time there pretty well but if I could, I’d like to suggest Three Dollar Dewey’s! It’s located in Old Port and is just the right mix of locals and tourists!
Not to take away from Portland but I can’t help but suggest that you come to my favorite town in the world-North Conway, NH!! We have all that Portland has plus, gorgeous views and superb skiing and snowmobiling too!
Happy travels and hope to meet you in North Conway someday!
Teena