Holiday festivities in DINE country – Part I, Massachusetts holiday events

Nautical Santa at Inn at Harbor Hill MarinaHoliday shopping season may have started before Thanksgiving, but what we like to call the Harvest to Holidays time of year is getting underway now.  The Distinctive Inns of New England (DINE) embrace the holiday season with beautiful décor, festive menu items and plenty of local events to bring on the joy of the season.  Plan your next romantic getaway to one of the nine DINE inns and you’ll enjoy a myriad of New England holiday events.  We’ve created this blog series to help with planning your holiday getaway.  Combine that with unique shopping and outdoor adventures at each of the DINE inn communities, and you’ll enjoy the perfect holiday getaway topped off with sumptuous breakfasts, crackling fires and guest rooms perfect for snuggling with your favorite Santa’s helper.

Here’s a rundown on the festive holiday events coming up at your favorite DINE inns in Massachusetts.

At Captain’s House Inn

Fireplace with two chairs in front of it and decorated mantle at Captain's House InnIt starts with the Chatham Turkey Trot on November 24, 2022 at 8:00 am, the perfect way to kick off a day of Thanksgiving eating. The Chatham Turkey Trot is a 5k (3.1 miles) run/walk event. There’s a $30 entry fee to support the Lower Cape Outreach Council.

In addition, Garden Aglow at the Heritage Museum and Gardens near the inn is a series of outdoor festive light displays to walk through Nov 22-Dec 23, 2022. Roast marshmallows by a campfire, enjoy lawn games and grab a bite to eat from Lilly’s Café or the Cape Cod Donut Truck. Purchase tickets in advance.

If you want to get into the holiday spirit book your holiday stay during Chatham’s Christmas by the Sea Stroll Weekend December 9 -11, 2022. There will be a light parade around downtown, the annual tree lighting ceremony, plenty of caroling, a visit from Santa, and more. Local businesses and restaurants will offer sphigh tea at Captain's House Innecial holiday menus, sales and deals.

Best of all, add a holiday high tea at the Captain’s House Inn to the festivities. You’ll indulge in a three-tiered platter of finger sandwiches, scones, pastries, and cakes. It’s always an excellent idea to warm up with a cup of hot tea on a cold winter day. Here’s the menu.

At Deerfield Inn

Bring the whole family and get in on all the holiday fun at this historic inn. A number of holiday events are in store at Champney’s Restaurant and Tavern to enhance a tour of Historic Deerfield and a stay in the inn’s beautifully appointed inns.  Rooms and suites vary from one to two beds, perfect for families traveling together.

It all starts with Thanksgiving dinner on Thursday, November 24, 2022 from 11:00am -6:00pm. Enjoy all your holiday favorites with full menu available too for the non-turkey eaters. Book online at ChampeysRestaurant.com. Reservations required.

Add a Carriage Ride to your stay, Saturday and Sunday afternoons 12:00-3:00pm on November 26 & 27 or December 4, 10, 11, 17&18th. Private 30-minute carriage rides are provided by Clay Hill Farm on Old Main Street in Historic Deerfield. It’s $60 for up to 4 people and then $5 for each additional person up to 8. Bring your own blankets and enjoy a wonderful outdoor activity. Reservations strongly suggested to guarantee your time 413-774-5587 Payment is taken at time of booking.

Santa Experience at Deerfield InnBring the children or grandchildren to the Deerfield Inn for dinner with Santa & Mrs. Claus on Dec. 4, 5, 6, 12, 13,  19 &20th  from 4:00- 6:00pm. For a little more jingle in the season, Santa & Mrs. Claus will join your table to share a story and listen to your children’s holiday wishes. The full children’s and regular dinner menu available with complimentary Mrs. Claus cookies. The Santa Experience is $25 in addition to your meal plus tax and 21% gratuity. Reservations are required at 413-774-5587 and unfortunately, to get Santa & Mrs. Claus back to the North Pole to feed the reindeer, the restaurant is not able to accept walk-ins for this event.

Now here’s a fun way to show off that holiday sweater you got last year! The Holiday Sweater Event will be Dec. 16th from  11:30am -9:00pm. Come dressed in your favorite Holiday sweater and receive 15% off your entrée in the restaurant while listening to live music with TJ & The Peepers from 6:00-9:00pm. Reservations are requested at 413-774-5587.

At Harbor Light Inn

Parlor at Harbor Light Inn with Christmas treeOne of the longstanding Massachusetts holiday events, and perhaps one of the oldest holiday celebrations in New England is the Annual Marblehead Christmas Walk. This  signature event captures the warmth of the holiday season throughout the entire town. Holiday time is when Marblehead’s historic charm shines bright, and the festive spirit of the holidays provide an enchanting experience starting with the Marblehead Christmas Walk.  Celebrating its 51st year, holiday revelers are encouraged to join the Marblehead Chamber of Commerce December 1st – 4th for this festive weekend including the tree lighting, Santa’s arrival by lobster boat, a parade, artisan markets, the Gingerbread festival, music and so much more.

It starts on Thursday, December 1st with a Holiday Shopping Preview Night. On Friday, December 2nd the  Annual Tree Lighting takes place, followed by Saturday, December 3’s Christmas Walk Parade. Stay through Sunday, December 4th for events and shopping throughout town. Read more here.

Harbor Light Inn tavern with two wine glasses on the barReturn to the inn after a day of holiday shopping and reveling in Marblehead and enjoy your favorite spirits or glass of wine in the tavern and then return to your beautifully appointed guest room for visions of sugarplums dancing in your head!

Better yet, book the “Sweeten Up The Season” enhancement package and revel in the season.  The package includes 2 holiday special cocktails from the tavern (or 2 splits of Champagne),2 Harbor Light Inn keepsake mugs with specialty hot chocolate, a Box of sweet sloops from local chocolatier Harbor Sweets in their festive holiday bag and a small lighted Christmas tree in the room to add festivity during your stay. The package is $75 in addition to your room charges and must be booked in advance.

Price $75

Next week, we’ll explore holiday happenings in other parts of DINE country. Plan to make the most of these holiday events by combining it with a getaway to your favorite DINE inn.  Don’t forget to book your stay directly with the inn.

In Connecticut: Inn at Harbor Hill Marina in Niantic

In Massachusetts:  Harbor Light Inn in Marblehead, Deerfield Inn in Historic Deerfield and Captain’s House Inn in Chatham on Cape Cod

In Maine:  Inn at English Meadows in Kennebunkport.

In Vermont:  Rabbit Hill Inn in Lower Waterford & Grafton Inn in Grafton

In New Hampshire: Manor on Golden Pond  in Holderness & Chesterfield Inn in West Chesterfield