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Here's your plan for enjoying festive drinks and holiday cheer at Boston's iconic Harpoon Brewery. Watch the video 👇

Home of New England’s original IPA, this iconic Boston brewery is now hosting a Christmas bar that is filled to the brim with holiday cheer!  

Holiday Pop Up Bar at Iconic Boston Brewery 

Visit Harpoon Brewery's Holly Jolly Bar for festive cocktails or classic brews, served in holiday mugs in Boston's Seaport neighborhood.

Christmas Cocktails

✅ Before you go
• Holly Jolly Bar is popping up between November 22 and January 4th this year
•  Your ticket includes the price of one drink, and every additional drink costs only $10-$12 extra! 
• Book your ticket here: https://bucketlisters.com/experience/holly-jolly-bar-at-harpoon-brewery

💪 Pro tips
• If you ask nicely, you can choose which fun holiday mug /  glass you want your drink to be served in! 
• Keep an eye out for the Dunkin’ collab on the menu 👀
• Grab a case of cold ones for your favorite homebody before you go! 

Enjoy Christmas cocktails, or classic brews on tap!

this Christmas bar is finally popping up in Boston and it's filled to the brim with

holiday cheer- just like you'll be, if you stop by!

You may already know Harpoon Brewery as the birthplace of New England's original IPA

with iconic institutions like Dunkin’ and L.L. Bean

it's decked out in decorations and fully stocked with cocktails in festive cups.

Whether you prefer a beer + bar bites, or drinking out of an ornament from the tree,

Holly Jolly Bar has something for everyone… even the homebodies!

Happy Holidays, and I'll see you at Harpoon.

Here's your plan for cheesy pizza, mozzarella sticks, wine, then beers and games at Notch Brewing. Watch the video 👇

Here’s your go-to night out in Allston-Brighton: start with massive mozzarella sticks and perfectly crisp pizza at FiDO, then keep the evening going with laid-back beers and games at Notch Brewing at the Charles River Speedway.


Cheesy Date Night 🍕🍻

FiDO Pizza in Allston serves up giant mozzarella sticks and crispy pizzas, plus a Thursday date night special with salad, pizza, and wine. Fun events like Jeopardy trivia, too!

Pizza & Wine

💪 Pro tips
• Check out their date night special on Thursdays: salad, pizza, and wine for $25 / person! 
• Every Sunday from 3 - 5 PM you can enjoy Jeopardy bar league trivia! 


FiDO Pizza 

Hang out at Notch Brewing in Brighton for laid-back beer, darts, and lively vibes. Try the blood orange radler for a fruity twist to your evening.

Beer & Games

💪 Pro tip
• Get the blood orange radler for a delicious, fruity beer! 


Notch Brewing 

Are you looking for your next cheesy date night?

They opened back in August and I finally got the chance to check it out.

We weren't able to make it on a Thursday,

but I spotted their date night special and it is such a good deal.

decided to kick things off with a little wine.

and I'm not exaggerating when I say they could have been a whole meal on their own.

They also have weekday specials and even a Jeopardy league.

Notch Brewing at the Charles River Speedway.

Here's your plan for exploring shops, savoring seafood, enjoying coastal views, and relaxing in Portland, Maine. Watch the video 👇

It’s the perfect short getaway when you want that cute, coastal town vibe with just enough happening to keep you exploring all weekend. Portland, Maine has that warm, welcoming energy — a small city with a big sense of community. It’s completely walkable, with charming streets lined with home and décor boutiques, lifestyle and clothing shops, local donut spots, and some of the best restaurants in New England.

Weekend Getaway to Portland Maine

Download the Umo app and select DiriGo for easy access to Greater Portland's public transit system, making it simple to get around the city.

Taking public transit

✅ Before you go
• Download the Umo App and Select DiriGo (Southern Maine) while setting up the app. This app is for greater Portland public transportation. 


Public Transportation

Stay in Old Port or nearby for boutique hotels, waterfront views, easy walks to shops, restaurants, and galleries—perfect for exploring Portland's vibrant charm.

Hotel Stay

✅ Before you go

Before you go:
Figure out what vibe you want before booking your stay
• Old Port: lots of boutique hotels, walking distance to everything, waterfront views, lively
• East End: more peaceful and neighborhood feel, close to Eastern Promenade (trailhead), along  5-10 minutes from downtown
• Arts District: runs along Congress street, filled with galleries, coffee shops, small theaters, vintage stores, eclectic and artsy atmosphere
• West End: more residential, historic architecture, 10-15 minute walk to downtown 


Overnight stay 

Start your day with a visit to Holy Donut in downtown Portland for fresh, fluffy, and allergy-friendly potato donuts. Arrive early for the best selection!

Eat donuts

💪 Pro tips
• Get there early because they sell out/have limited options by end of day
• Very allergy friendly- gluten free and vegan options 


Holy Donut

Browse high-end, sustainable, and modern resale clothing, shoes, and bags at Haberdashery Resale Clothing. Follow their Instagram @haberdasheryportland for new arrivals.

Clothing shopping

✅ Before you go
• Check out their Instagram page for new pieces @haberdasheryportland

💪 Pro tips
• They ship nationwide! 

Haberdashery Resale Clothing

Browse an eclectic mix of local trinkets, vintage finds, vinyl records, and unique gifts at The Merchant Company in downtown Portland.

Vintage & Trinket Shopping

💪 Pro tips
• Take your time here- there is such a variety of goods (knickknacks, vintage, vinyls, antiques, cosmetics, etc.)

The Merchant Company

Enjoy classic Maine lobster rolls, fries, and oysters at The Highroller Lobster Co. Perfect for a casual lunch or takeout right in downtown Portland.

Lobster rolls & fries

💪 Pro tips
• They offer takeout options- walk up to the gift shop counter to place your order 


The High Roller

Browse Baske for high-quality, modern home decor and unique, colorful pieces to elevate your living space during your Portland getaway.

Home decor shopping

💪 Pro tips
• Beautiful place if you’re looking for high quality modern items

Baske

Explore Blanche + Mimi for a curated mix of new and vintage eclectic pieces from around the world—perfect for those seeking unique home goods and gifts in downtown Portland.

Curated goods shopping

💪 Pro tips
• Head here for a mix of new and vintage eclectic pieces from around the world 

Blanche + Mimi

Enjoy delicious Italian cuisine and craft cocktails at Via Vecchia in downtown Portland. Make a reservation for dinner and don't forget the must-try chocolate gelato!

Italian Dining & Wine

💪 Pro tips
• Highly encourage booking a reservation for a weekend night! Walk-ins are accceptable but not guaranteed seating in a timely manner.
• Very accommodating for dietary restrictions
• The chocolate gelato is a must!


Via Vecchia

Grab fresh artisan breads and pastries at Standard Baking Company. Enjoy quick service, outdoor seating, and check allergen info online before you order.

Fresh bread & pastries

✅ Before you go
• Usually there is  a line out the door during busy hours, but moves very quickly once you are indoors 
• There are outdoor tables and benches for eating 

💪 Pro tips
• Look at their basked goods online prior to ordering to see the allergens for each item (https://standardbakingco.com/shop/)

The Standard Baking Company

Visit Portland Head Light in Cape Elizabeth for stunning ocean views and a scenic walk around historic Fort Williams Park. Ideal for photos and learning about local history.

Scenic Walk & Views

✅ Before you go
• Stop here on your way back to Boston!

💪 Pro tips
• Take a walk around the water and learn about the history of Fort Williams Park


Portland Head Light

Here's your plan for a quick weekend getaway to Portland,

You can drive 2 hours or take a 2.5 hour train ride

with rideshare and bus options from the station to downtown Portland.

with lots of boutique hotels and Airbnbs right in the heart of it all.

First stop is the Holy Donut in the Old Port for fluffy,

Just 4 blocks away is the Haberdashery for sustainable,

Next up is The Merchant Company in the Arts District.

The 15 minute walk is worth it for the best local trinkets,

You'll then stroll down Congress Street to the high roller back in Old Port for fries,

Bask is next on the list for clean and colorful home decor,

and Blanche and Mimi for curated goods from around the globe.

but the food and drinks are the main event.

you can't go wrong with anything on the menu,

you'll walk to the Standard Baking Company right in town.

They've got an endless list of fresh bread and pastries made daily.

stop at the Portland headlight just 15 minutes south in Cape Elizabeth.

The ocean views are incredible all year round.

all you gotta do is pick a weekend and make it happen.

Here's your plan for grabbing pastries at Tatte and exploring Harvard's Natural History Museum. Watch the video 👇

Visit an amazing science museum and treat yourself to something at Tatte!


Natural History Museum 🦕

Relax at Tatte in Harvard Square and enjoy pastries and specialty lattes, like the pistachio latte, before heading to your next adventure.

Coffee or pastries

✅ Before you go
• Lots of seating upstairs and downstairs if you want to relax before the museum.

💪 Pro tips
• Get the pistachio latte… there’s crushed pistachios on the bottom!

Coffee or pastries at Tatte ☕️

Explore fascinating exhibits on gems, botany, and sea life at the Harvard Museum of Natural History—one ticket includes the Peabody Museum too!

Natural history exhibits

✅ Before you go
• Purchase tickets once you get there: https://www.hmnh.harvard.edu/plan-your-visit

💪 Pro tips
• Save time to check out the glasswork exhibit!
• The museum is connected to the Peabody Museum of Archaeology & Ethnology, and admission to one museum admits you to both during regular hours.

Harvard Museum of Natural History

If you'd like to learn new things or just like a

plan that includes staying inside when the weather is crappy,

My boyfriend and I went to Cambridge for the day,

We walked to the Museum of Natural History,

They have a variety of exhibits ranging from gems to botany

My boyfriend is obsessed with sharks and really loved the shark exhibit.

Here's your plan for a luxurious staycation with butler service and spa amenities in historic Back Bay. Watch the video 👇

Enjoy the city's only butler service and an elevated staycation nestled right in historic Back Bay. Perfect for a special occasion 

An Elevated Staycation Experience in Back Bay

Elevate your staycation with Raffles Boston's butler service, spa amenities, and customizable in-room comforts in the historic Back Bay.

Luxury Staycation

✅ Before you go
• Book your stay: https://www.raffles.com/boston/
• Bring your bathing suit - you'll definitely want to take advantage of the included spa amenities 

💪 Pro tips
• You can literally pick what snacks and pillows you want in the room before you go - definitely try out the lavender pillow! 
• Be sure to snag a res at the Blind Duck for date night or Long Bar Terrace for a nice dinner! If you book when it's warm out, snag an outdoor seat for the best views 