How To Celebrate The Holidays in Boston

Outfit Gifted by Pearl by Lela RoseSweater: Pearl by Lela Rose (c/o) Skirt: Pearl by Lela Rose (c/o) Tights: Spanx (my winter go-to for skirts and dresses!) Boots: Sam Edelman (past season, same style in suede available)

It’s the most wonderful time of the year!

Christmas is my fave fave fave and I love how festive and decked out things get here in Boston. I always look forward to the day when the big wreaths go up on the Boston Public Library and there’s nothing cozier than grabbing a drink in one of the super festive hotels downtown. If you are getting ready for the holiday season here in Boston, here’s a list of some of the best ways to get in the spirit- from shows to tree lightings to kid friendly events- I’m sure you’ll find the perfect way to celebrate with your family and friends.

Before I get into all the Christmas things, just have to mention this outfit from the most recent Pearl By Lela Rose collection. The Pearl by Lela Rose team was kind enough to gift me this look for the holidays and I love it. The sweater is covered in pearls– my dream!- and the windowpane skirt is perfectly festive, but could easily be worn beyond the holidays. I know I’ll be wearing this look multiple times over the holiday season. In fact thinking about this sweater for our family photos. It’s a classic!

All I want for Christmas… is to go to a festive show!

Boston Ballet’s The Nutcracker– The Nutcracker is back this year running from November 29th to December 29th. I’m so excited to go back! It’s the perfect girl’s night and excuse to get dressed up in your holiday finest while sipping champagne in the truly stunning Boston Opera House.

Boston Symphony Orchestra Holiday Pops– Another favorite in our house 🙂 MJD loves the Pops and we’ve been several times. It makes for a great pre-Christmas date night. There are also kid friendly matinees and shows if you want to bring the little ones. Runs from November 30th to December 24th at Symphony Hall.

Dolly Parton’s Smoky Mountain Christmas Carol– If you are looking for a change from your standard holiday show this year, may be check out Smoky Mountain Christmas Carol. This play takes the classic Ebenezer Scrooge story and sets in in East Tennessee with music from Dolly Parton. The show is playing at the Colonial Theatre from December 3 to 29th.

Oh Christmas Tree, Oh Christmas Tree Lightings

Copley Square Tree Lighting– December 2nd at 5 PM. There is a family friendly party after at the Fairmont Copley that is free for anyone to attend.

Boston Common Tree Lighting– December 5th at 5 PM. There will also be an ice skating show at the Frog Pond rink to celebrate!

Seaport Tree Lighting (and Stroll!)– December 6th from 5-9, with tree lighting at 7 PM. Besides the tree lighting, this is the Seaport’s first holiday stroll which will include special treats at stores and also a festive acapella performances on the Seaport Common.

Beacon Hill Tree Lighting and Stroll– December 6th with stroll from 6 PM to 9 PM. The Beacon Hill holiday stroll is always busy, but always fun. Charles Street is shut down to traffic and the stores offer many treats and refreshments to help with your holiday shopping. A holiday highlight for sure!

Baby, It’s Cold Outside… Let’s stay inside and have a drink 🙂

Boston Public Library’s Courtyard Tea Room Holiday Tea– The tea at the BPL Courtyard Tea Room is amazing already, add a festive flair to it and you’ve got a great way to celebrate with the ladies in your life. Reservations required, the holiday menu is available from November 27th through December 30th.

Drinks at The Liberty Hotel– The Liberty is known for the upside down Christmas trees hanging in their lobby, making it a fun and festive place to grab a holiday cocktail. It’s very convenient to Beacon Hill if you are looking for somewhere to go post- stroll as well 🙂

The Hot Cocoa Bar at the Ritz’s Avery Bar– Cozy up by one of the fireplaces for a mug filled with hot cocoa (spiked or not) and sweets! The Hot Cocoa Bar is open every Saturday from December 9th to December 30th.

The Lenox Hotel Lobby A few holiday seasons ago I went to an event at The Lenox and let me just say their lobby was the coziest place ever! It honestly felt like you were in just a gorgeously decorated home getting ready to celebrate the holidays. This would be the perfect place for a quiet, romantic cocktail.

Santa Claus is coming to town… and taking the kids out to celebrate!

Sugar Plum Fairy Tea at the Ritz Carlton- I imagine a young girl would swoon over having tea with characters from The Nutcracker while having lunch at a beautiful city hotel. This tea only happens twice so I am sure it books up quickly- dates are December 10th and 17th!

Zoolights at Stone Zoo– This event is on my list to visit with Nicholas! Stone Zoo turns into a winter wonderland decked out in lights from November 22nd to January 4th.  You can also have hot chocolate with the reindeer and get your picture taken with Santa too!

Breakfast with Santa at The Shops at Chestnut Hill– Tickets are now on sale for breakfast with Santa at The Shops at Chestnut Hill. The morning includes arts & crafts, story time with Santa and breakfast from The Cheesecake Factory.

Edaville Express Santa Train Ride– The Edaville Express is a 45 minute train ride with Santa, Mrs. Claus, elves complete with cookies and milk and Christmas carols. I think we will be doing this once Nicholas is a bit older! This is not technically in Boston, but it sounds like it would be worth the ride 🙂

While many of the ideas I listed in this post require advance reservations and could be on the pricey side, Boston gets so festive for the holidays you can easily enjoy it no matter what. Grab a hot cocoa from Starbucks, take a stroll around Back Bay (check out the BPL’s wreaths or the Cartier store on Newbury where I took these pictures) or hop over to Beacon Hill to see the amazing holiday decor lining the neighborhood.

Will you be celebrating the holidays with any of these festive activities? I’d love to hear all about your plans!

xoxo, Jenna





  1. November 20, 2019 / 10:26 am

    Beautiful outfit! I love your ideas as well!

    • Jenna at Boston Chic Party
      December 3, 2019 / 4:47 am

      Thanks so much, Danielle! xoxo!

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