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25 Ways to Celebrate the Holidays this Season

November 20, 2019

We. Are. So. Excited! The most wonderful time of the year is finally upon us. You know? The time of year for ugly sweaters and Mariah Carey all day every day? Hot chocolate with extra mallows and Love Actually on repeat. We love Christmas. And lucky for us, there are so many ways to savor each magical moment this season with your families.  Make some memories, start a new family tradition and tap into the magic of the season at any one of these holiday experiences throughout Greater New Haven.

Did we miss something?  We'd love to hear from you! Email makaylasilva@macaronikid.com

1. Grab a thermos of hot cocoa, hop into the car and take a drive through a wonderland of lights—New Haven
Fantasy of Lights is an annual tradition in the Elm City. Open mid-November until after Christmas. 

2. Take a trolley at the Santa's Trolley Winter Wonderland—East Haven
Ride along the Connecticut shoreline on a historic trolley decorated for the season and make lasting memories with your children. You'll get to stop and visit Santa in a historic trolley car. No reservations needed, trolley comes every 20 minutes.

3. Celebrate Winter with The Shops at Yale—New Haven
So many things to do at this FREE event. Take a horse drawn carriage ride, see six professional ice-carvers, sample hot cocoa from the best New Haven chefs, hear Santa read a story, listen to carolers and so much more!

4. Lace up your skates and spend an afternoon on the ice—Milford
Milford Ice Pavillion offers free skating on the weekends. Rentals are available.

5. Pick a pine tree at Lou's Tree Farm—Orange
Lou's is our family favorite for cutting down your own trees. This tucked-away tree farm has been in the same family for generations. It's small but if you ask us, it's just right.

6. Annual Holiday Gilbert Train Exhibition at the Eli Whitney Museum -  Hamden
The Eli Whitney Museum's annual hands on exhibition of American Flyer Trains opens , Friday November 29th at noon. 

7. Get toasty by the fire at the Firelight Festival — Guilford
Spend an evening at Connecticut’s oldest house with festive luminaria, lanterns, and outdoor fires. Roast marshmallows, enjoy popcorn, mulled cider, and some delightful readings of the The Night Before Christmas at Henry Whitfield State Museum. There are also self-guided tours of the 1639 Whitfield House after dark, the telling stories of the origins of Christmas traditions in the Holidaze display, and crafting pine cone ornament crafts.

8. It's not Christmas without Rudolph!—New Haven
Rudolph the Red Nose Reindeer is this year's children's production for the holidays at the Shubert Theater. Running time is 90 minutes.

9. Have brunch with Santa at the Madison Beach Club—Madison
Choose from a delicious breakfast menu while 

10. Christmas in Europe - New Haven
From November 16, 2019 to February 2, 2020 the museum will exhibit more than 80 Nativity scenes or crèches, icons, and religious artworks representing 30 countries across Europe, including its signature 120-square-foot Neapolitan (Italian) crèche.

11. Christmas Shopping at Maple View Farm - Orange
Maple View Farm will feature craft vendors for your gift giving pleasure on Sunday, December 1st. Come and visit and buy home made from talented artists.There will have items for everyone in your family, including outfits for your pets don’t forget to bring your pets measurements as Royal Tail Coats will be here, jewelry, fiber from the farm Children’s dresses, Thirty One bags, and much more!

12. Jingle All The Way to Breakfast with Santa - Milford
Enjoy pancakes, hot chocolate, crafts, caroling, face-painting and, of course, Santa! Sun Dec. 8th 9am - 12pm, $7/per person.

13. Storytelling with Santa - New Haven 
Santa will visit The Shops at Yale and read stories to children and take photos with families from 1:00-3:00pm. Free and open to the public. Snacks will be provided.
–Saturdays: Nov. 30, Dec. 7, 14 and 21 at The Yale Bookstore, 77 Broadway. Snacks provided by Katalina’s Bakery!
–Sundays: Dec. 1 and 22 at Willoughby’s Coffee & Tea, 194 York Street.
–Sundays: Dec. 8 and 15 at Claire’s Corner Copia, 1000 Chapel Street.

14. Visit Santa at the CT Post Mall - Milford
Guests of all ages are invited to visit Santa and enjoy a new interactive experience inspired by the fan-favorite Warner Bros. Pictures and New Line Cinema's film “Elf.”  The new walk-through set incorporates many of the most famous scenes from the film, while combining the best elements of today’s highly popular “selfie museums” and augmented reality interactive experience. The journey to see Santa has just become as much fun as the visit itself!

15. Take a Magical Horse & Carriage Ride - New Haven
Hop-On/Hop-Off on the Corner of College & Chapel Streets on College Street, (across from Claire’s Corner Copia, 1000 Chapel Street) and at the corner of York Street and Elm Street (across from Patagonia and GANT).
Saturday, December 7 (don’t forget to visit the Ice Carving Competition)
Sundays, December 1, 8, 15 and 22

16. The Gingerbreads of Broadway - Milford
A delicious new holiday musical and backstage legend! From vaudeville to Broadway, meet the Gingerbread Family! With the help of Mrs. Claus, Christmas dreams really do come true. Chock full of music and dance, The Gingerbreads of Broadway is a delightful new holiday confection, perfect for the entire family!

17. The 3rd Annual Christmas Tractor Parade - Orange
Join The Town of Orange for the 3rd annual Christmas Tractor Parade before the town tree lighting. If you’d like to participate in the parade, put some lights on your tractor and meet us at the Orange Fairgrounds Sunday December 1st at 4:00pm. The parade will leave the fairgrounds at 4:30 and travel to the town green for the arrival of Santa and the tree lighting. 

18. Cookie Decorating - Milford 
Bring your sweet tooth! Stop by and decorate some holiday cookies at ShopRite of Milford. Saturday, December 14th, 2019 Cost: $10 Time:11am-12pm &; 12:30pm-1:30pm

19. Christmas in the Mansion - Milford Delight in the seasonally decorated Mansion and hallways, visit Santa’s Workshop and enjoy treats from the Food Court. This community event, which raises funds for scholarship and programming, offers something for everyone on your gift list and so much more! Admission to event is $10 per person ; children under 12 free 

20. Stuff-a-Reindeer! - West Haven 
Head to Picasso Parties to stuff a reindeer with Santa on Dec. 22nd at 4:30pm. $20/child. Free hot chocolate!

21. Lamplight Stroll - Milford
Head Downtown Milford for a nostalgic New England Tradition at the annual Lamplight Stroll. The stroll begins on Friday December 6th at 6pm at the River Street Parking Lot with over 25 shops offering refreshments and holiday shopping. There will be horse and buggy rides, carolers and chirrups performances and a visit from Santa himself!

22. Storytime with Santa - Milford
Visit the Milford Regional Chamber of Commerce on Thursday December 5th at 4pm for a very special storytime with Santa. Don't forget your cameras -- this will be a wonderful photo opportunity!

23. The Learning Station: A Children's Holiday Journey - Milford
The Learning Station is an award-winning children's recording and performing company that has been rocking the children's music world for decades. This annual Christmas concert is back at Matthewson Elementary School on Saturday Dec. 7th at 11am. 

24. Children's Holiday Workshop - Decorate Your Own Gingerbread House - New Haven 
Please join us for our Annual Holiday Workshop- Children Welcome! Included with your ticket is a homemade gingerbread house, icing and assorted candies. Wine and Light Bites will be provided for Adults. Boxed Lunch for Children. Tickets are $60.00 for Adults and $45.00 for Children and can be purchased by calling (203) 467- 2531.

25. Storytime and Activities - Milford
Head to Barnes & Noble in Milford for a holiday storytime on Saturday mornings at 11am for holiday Storytimes featuring Dear Santa and Cookies for Santa.  on Nov. 30th and How the Grinch Stole Christmas on Dec. 7th. A special evening storytime on Friday Dec. 6th at 7pm will feature cookies, hot chocolate and The Polar Express.