12 Holiday Happenings to Enjoy in Boston and Beyond for 2018

The holiday season is upon us once again and with it comes a ton of fun and special events to enjoy in Boston and beyond! From time honored traditions to new special events, there is sure to be some festive fun for you and your favorite date to celebrate together this time of year. Check out some of our seasonal favorites this year listed below.


Photo Credit: Fanueil Hall Marketplace

1. Faneuil Hall

Stroll through Faneuil Hall and enjoy the festive atmosphere together.  From the beautiful seasonal decorations, outdoor performers, and shopping it is Boston welcoming the winter season at its best! Faneuil Hall is also home to the biggest Christmas Tree in Boston and is a must to check out during the holiday season. They also have Blink! a fun evening light show featuring the signature holiday tree along with other thousands of lights in the marketplace twinkling along to the tune of holiday pops from 4:30-10:30 daily.  Santa will also be strolling around for Santa Selfies on certain days.  Throw in dinner or a night cap at one of the many fabulous restaurants in the area and you will have a classic holidays in Boston date done right.
4 South Market Building, Boston


Photo Credit: Boston Frog Pond (facebook)

2. Boston Common

With the Boston Common as your backdrop, skating on the Frog Pond is a classic winter activity in Boston! Treat yourselves to some nostalgic holiday fun with ice skating and hot cocoa after at the Frog Pond cafe.  The Boston Common is beautifully decorated and lit up for the holidays and a visit to the Boston Christmas Tree on the common is a must. This tree is a yearly gift to Boston from the people of Nova Scotia and sparkles with thousands of twinkling lights. A stroll through the Boston Common is classic holiday time in the city!
Boston Common Frog Pond

Photo Credit: No. 9 Park

3. Holiday Lunch

Make time during the week to get together for a special holiday lunch for two. We always love celebrating special occasions at No. 9 Park and with their location right across from the beautifully decorated Boston Common the holidays season is an extra special time to dine there. This iconic Boston restaurant has a special holiday lunch featuring a 5 course tasting menu. The holiday lunch at No 9 Park is offered weekdays from 11:30-2 until December 21st.  Check out the details here for a fabulous Boston holiday lunch experience!
9 Park Street, Boston


Photo Credit: Assembly Row at Assembly Square (Facebook)

4. Ice Sculpture Stroll

Enjoy a festive night at Assembly Row on December 6 from 6-8 and discover 9 ice sculptures throughout the property along with music, treats, giveaways and other festive fun. They will also have holiday music every Saturday by Boston Free Radio through December 22nd. Check out the details for this event and other fun festive events hosted during the holiday shopping season here.
355 Artisan Way, Somerville

Photo Credit: Outlook Kitchen and Bar

5. Igloo Fun

The Lookout Rooftop Bar at the Envoy Hotel is once again having their pop up igloo bar this season! Located in the seaport district, you can enjoy amazing Boston harbor and city night views while cozily ensconced in your own little rooftop igloo. This festive pop up bar has 6 heated igloos including fleece blankets to add to the cozy and bright feeling. The igloos are typically first come, first serve and can comfortably fit 6-8 people.  To order a drink, guests need only to press a button and their igloo illuminates to notify the server. A fun and festive way to grab a holiday cocktail or two!
70 Sleeper Street, Boston

Photo Credit: SoWa Boston (facebook)

6. Festive Shopping

Holiday shopping dates are a must this season! If you can, be sure to check out the Winter Festival at SoWa for the biggest winter shopping village and holiday festival in Boston.  The festival is held over two weekends from November 30 – December 9. Shop local and enjoy winter cocktail specials, ice sculptures, food trucks and more. Check out the details here and plan a fun holiday shopping date soon!
450 Harrison Ave, Boston

Photo Credit: Heritage Museums and Gardens

7. Gardens Aglow

A date to take in a special holiday light experience is a must to get into the festive spirit! We love the Heritage Museums and Gardens special Gardens Aglow event where their beautiful grounds are decorated with amazing twinkling light displays.  There is also indoor holiday decor and festive activities throughout the galleries. The event runs from November 23 through December 30th.  The Heritage Museum and Gardens is in Sandwich and worth the trip for this beautiful display – check out our article here on things to do while in Sandwich to make a special evening or weekend of it!
67 Grove Street, Sandwich

Photo Credit: Tower Hill Botanic Garden

8. Night Lights

More magical light displays worth the trip for you and your date! The Tower Hill Botanic Garden hosts Day Lights and Night Lights in their winter holiday lights event. It is truly an enchanting experience meandering throughout 15 acres of their beautifully lit gardens and woodlands. There are also fire pits for cozying up with your date and a hot cocoa or adult beverage or two! This is a ticketed even from November 23-30th and peak times often sell out.  Check here for more information and to plan your holiday lights night out.
11 French Drive, Boylston

9. Enchanted Village

Take a nostalgic tour through the original Enchanted Village display together!  A Boston holiday tradition originally on display at Jordan Marsh department store in Downtown Crossing for many years is now permanently housed at Jordan’s Furniture store in Avon. The Enchanted Village still endears with its portrait of holiday times of yesteryear.  The old automated figures and scenes are a throwback and they even add in “snow” periodically as you walk through the display to holiday music.  Jordan’s Furniture also sells the famous Jordan Marsh blueberry muffins (using the original recipe) while the Enchanted Village is on display.  Along with the Enchanted Village display, there is also lots of fun holiday activities to check out here from a holiday music laser light show to a 4D Polar Express movie ride.  This is a great nostalgic holiday date or also a fun family holiday date tradition!
100 Stockwell Drive, Avon

Photo Credit: Hotel Marlowe

10. Miracle Bar

Set a date for a festive holiday night cap with your favorite this holiday season! Kimpton Hotel Marlowe is hosting their yearly Miracle pop up bar in its lobby this season from November 23rd through Saturday December 24th. Enjoy seasonally themed cocktails and snacks in a very fun and festive setting. An enchanting way to get some holiday cheers in together!
25 Edwin H. Land Blvd, Cambridge

11. The Nutcracker

A night out to see a performance of The Nutcracker is a classic holiday date. It is a truly magical and enchanting tale for all ages. The Boston Ballet’s production of The Nutcracker is a must see during the holiday season in Boston. It is performed at the beautiful Boston Opera House in the theater district offering a variety of places to also grab some dinner and drinks to round out your holiday night out. Check out Serafina which is nearby and offers theatre goers a complimentary tiramisu dessert for two when you present your ticket stub!
539 Washington Street, Boston

12. Holiday Tea Time

Take a break from the hustle and bustle to schedule a tea time for two this holiday season! There are many special holiday tea times in Boston but one of our favorite picks is a Champagne Afternoon Tea time in the Lobby Lounge of the Mandarin Oriental. Offering a fancy retreat from the cold complete with cozy fireside ambience, this Champagne Tea will serve holiday inspired pastries, teas and cocktails daily from 2-5pm until January 6th.  A little champagne along with your tea may be just what you and your favorite date need to get into the holiday spirit! Check here for details and to book your tea time.
776 Boylston Street



Photo Credit: Tower Hill Botanic Garden


Feature Image Credit: Tower Hill Botanic Garden

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