20 Holiday Happenings to Enjoy in Boston and Beyond for 2019

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.

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.  Performances are every half hour and the official Blink! treat lighting is December 3rd!  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: Faneuil Hall Marketplace

2. Illuminus 2019

The weekend of December 5th and 6th the Downtown Boston Business Improvement District along with LuminArtz will turn city streets into a fun and festive urban canvas and bring free protected artworks performances and immersive experiences to Downtown Boston! This free night time festival will have immersive art installations on building, kid friendly exhibits and more. The perfect festive enhancement to weekend shopping and dining in the Downtown area to kick off the holiday season.
begins at 100 Summer Street, Boston

Photo Credit: Downtown Boston BID

3. 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! This year the Boston Common Tree Lighting will take place on December 5th from 5-6pm along with a Skating Spectacular show on the Frog Pond with local favorites performing on the ice!
Boston Common Frog Pond

Photo Credit: Boston Frog Pond (Facebook)

4. 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 this year is offered December 2nd to the 21st, Monday – Friday, from 11:30-2pm (& Saturday, December 21st).  Check out the details here for a fabulous Boston holiday lunch experience!
9 Park Street, Boston

Photo Credit: No. 9 Park

5. Ice Sculpture Stroll

Enjoy a festive night at Assembly Row on for their 3rd Annual Ice Sculpture Stroll December 5th from 6-8pm. Follow a map to discover the ice sculptures and treats while enjoying music, giveaways, and a holiday memento upon completing the map! 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: Assembly Row at Assembly Square (Facebook)

6. 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. This year, Lookout is also debuting a new heated enclosure of the main bar as well! A fun and festive way to grab a holiday cocktail or two!
70 Sleeper Street, Boston

Photo Credit: Outlook Kitchen and Bar

7. 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 5th Annual SoWa Winter Festival will be December 6th-8th. Shop local and enjoy winter cocktail specials, live ice sculpting, food trucks, holiday workshops and more. Check out the details here and plan a fun holiday shopping date soon!
450 Harrison Ave, Boston

Photo Credit: SoWa Market (Facebook)

8. 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 Friday, Saturday, and Sunday from November 29 through December 29th. This year guests can experience expanded lighting displays and outdoor interactives!  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: Heritage Museums and Gardens

9. 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 event and peak times often sell out.  Check here for more information and to plan your holiday lights night out.
11 French Drive, Boylston

Photo Credit: Tower Hill Botanic Garden

10. 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

11. Sippin’ Santa

This year Shore Leave will completely transform itself for the holiday season with its Pop up: Sippin’ Santa! November 26 through New Year’s Eve a whole new menu of signature holiday cocktails will arrive as well as nostalgic Christmas decorations and a soundtrack of holiday songs. A fun tropical twist on Santa!
11 Willam E Mullins Way, Boston

12. 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 29th through Saturday December 24th.  Enjoy seasonally themed cocktails and snacks in a very fun and festive setting as their Lobby Bar transforms into a winter wonderland of cheer.  An enchanting way to get some holiday cheers in together!
25 Edwin H. Land Blvd, Cambridge

Photo Credit: Hotel Marlowe

13. 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.
539 Washington Street, Boston

14. 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 this year is the Santa’s Workshop Tea in the Lobby Lounge of the Mandarin Oriental. Offering fun for adults and children alike, the kids can participate in a craft or other activities while adults sip on champagne, teas, savory bites and sweet treats daily. This special seasonal tea will be offered daily from 2-5pm from November 30th until December 30th.  A little champagne along with your tea may be just what you need to get into the holiday spirit! The hotel also encourages guests to bring a toy or game to be donated to Franciscan Children’s and those who donate will enjoy a decadent chocolate fountain bar in addition to the Afternoon Tea. Check here for details and to book your tea time.
776 Boylston Street

Photo Credit: Mandarin Oriental Boston

15. Light Up Seaport

The Seaport neighborhood will have its 4th annual tree lighting on Friday, December 6th from 6-8pm.  Enjoy interactive art installations, live holiday tunes, and more.  There will also be the first ever Holiday Stroll from 5-9pm with participating stores open to provide hot chocolate, cookies, and more!

16. Zoo Winter Wonderland

Southwick Zoo will transform into a Winter Wonderland from November 29th through December 29 on Fridays, Saturdays, and Sunday.  Ride a train through a forest of holiday light displays, visit with Santa at his house, and meet Santa’s furry friends in the petting zoo! There will be live entertainment, treats from the Gingerbread Baker and Cirque de Holiday performance (in a heated tent) featuring acrobatics, holiday magic, jugglers, and more.  Also be sure to stop in to Galliford’s Tavern next door for seasonal New England style food and drink – as well as a cozy fireplace and views of the Zoo!
2 Southwick Street, Mendon

17. Cookie Swap

Flour Bakery will host its 10th Annual Cookie Swap on December 14th from 3-5pm. Cookie makers from the community bring two to three dozen of their favorite holiday cookies  and all proceeds from the event this year will go to Catie’s Closet. Catie’s Closet is a local non-profit organization that provides the basic necessities of clothing and toiletries to students in grades K through 12 who are living in poverty or experiencing homelessness. Flour provides drinks, pastry boxes, and all participants get a recipe book as well! Click here for tickets and more information!
Flour Baker + Cafe
19 Drydock Ave, Boston

18. Gingerbread House Decorating

The Fairmont Copley Plaza will host gingerbread decorating party for adults on December 10th from 7-10pm! Each ticket include one gingerbread house, decorations, assistance from the culinary team, wine, beer, festive holiday cocktails and canapes! Get in touch with your inner child and enjoy the simple joys of some classic holiday cheer! Click here for tickets and more information.
Fairmont Copley Plaza
138 Saint James Avenue, Boston

Photo Credit: Downtown Boston BID

19. Copley Tree Lighting

The Copley tree lighting ceremony will take place December 2nd at 5pm and after the ceremony the Fairmont Copley Plaza will host a reception with cookie decorating and photos with Santa. There are also lots of great restaurants to head into warm up from the cold afterwards including the Oak Long Bar + Kitchen right in the Fairmont Copley Plaza!
Copley Square, Boston
Fairmont Copley Plaza
138 Saint James Avenue, Boston

20. Winter Skate at Patriot Place

Patriots Place, right outside Gillette Stadium, has opened their outdoor Winter Skate arena for the season and it is the perfect classic winter date fun.  The Pats play here but there is so much shopping, dining, and more here that the addition of a skating rink is the perfect festive touch to any date here! The MBTA also now has daily service here from Boston.  They will also host a Giving Tree lighting on November 29th which will feature a pyrotechnic reveal! So much holiday cheer to discover in one spot here!
Patriot Place
2 Patriot Place, Foxborough

Champagne Toast



Feature Image Credit: Mandarin Oriental Boston (Afternoon Tea)

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