10 Annual Family Traditions

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Most people who know me know I am a BIG planner; even quarantined during a pandemic, I keep a calendar and a running list of future plans and activities. Many 2020 activities had to be cancelled or rescheduled, but I am sure we are collectively hoping 2021 will bring more opportunities for adventures. Chances are, lots of people will be eager to get out and start exploring again.

This week, we’re sharing a few of our favorite traditions in the hopes that they return for 2021. Several of these activities require reservations and tickets often sell out quickly, even in a few minutes, so mark your calendars and set an alarm to remind yourself! I’ve also included two NEW-to-us ideas for 2021:

January: The Train Show at New York Botanical Garden is one of our favorite traditions. Usually housed inside the Haupt Conservatory, the train show includes dozens of tracks that crisscross through the various plant exhibits and the nearly 200 recreated New York landmarks replicated using natural materials. This year, the exhibit is showcased in a large, heated (and ventilated) tent, which allows for more aisle space. Our kids love the lady bug and bee themed trains. It truly is a magical event that ALL ages will enjoy.
When to reserve tickets: Tickets usually go on sale in late September or early October. 
Travel tips:  The event is held outdoors and it usually takes 60-90 minutes to walk through the exhibit. Even though this is a “holiday” event, we like going the last week or two (usually the first 2 weeks in January) because the crowds are significantly smaller. If you go in December, try and get tickets for the first hour it’s open.
Read about our adventures at and travel tips here
Note for 2020 season: Due to pandemic restrictions, the Train Show is only open to members of the NYBG. We’re lucky enough to have a membership and plan on attending. If you are not currently a member, consider joining! The NYBG has programs and events all year long that are very family friendly.

February: Take a chocolate making class. I am hoping to make this a new tradition, now that my kids are a little older. There are several shops in Connecticut that specialize in gourmet chocolates, like Bridgewater Chocolates, in Bridgewater and Le Rouge Chocolates in Westport. I have been hearing great things about the classes at Fascia’s Chocolates in Waterbury and plan on taking the kids for a class in 2021. 
When to reserve tickets: Most shops offer a monthly calendar online; check ahead for special themed classes based on interest or ingredient. 
Travel Tips: Be sure to let the company know of any allergy concerns ahead of time, and eat before you go so you’re not ravishing and overeat!

May: The Essex Rail Trail bike was one of our (new) favorite activities of 2020! There are 4, 6, and 9 mile trails and guests can pedal a two person or four person bike. Some of the trails run through alongside the Connecticut River, and the scenery is beautiful! For 2020, reservations started in late spring and ran through November. The rail trail is expected to open early in 2021 due to its immense popularity in 2020 and I have heard rumors that additional trails will be added.
When to reserve tickets: I would start checking in March. In 2020, tickets sold out quickly, especially on the weekends. The Steam Train Authority did a great job of adding dates and times, so be sure to check the website frequently. Spring blooming or fall foliage would be especially picturesque.
Travel Tips: Put on sunscreen and bug screen ahead of time, and use the restroom before you arrive. Bring a bottle of water (there are cup holders on the bikes).

June: In Connecticut (and probably throughout the country), June is the start of fruit picking season. Strawberries usually ripen in June, blueberries and raspberries ripen in July, peaches ripen in August, and apples are ready in September and October. 
Travel tips: Wear sunscreen, bug spray, sneakers and bring water, especially on hot days. Use the restroom at home before you leave, as most farms only have portapotties. Many farms offer free recipe cards, so be sure to ask if you don’t see sheets near the check in area. We like to pick fruit first thing in the morning before it gets too hot. Most trails take an hour to complete.
Find a list of farms and picking seasons in Connecticut here

July: Smell the lavender at Lavender Pond Farm in Killingsworth, Connecticut. The 25 acre farm has over 10,000 lavender plants that are harvested in nearby Old Saybrook and then grown on site. Visitors are welcome all summer to explore the grounds and follow the Lavender Labyrinth for free. Kids will love following the path around the pond to search for fairy houses and taking a trip on the lavender train, a 25 minute guided tour around the farm  .
When to go: First thing in the morning, before the farm gets too crowded and the temperature gets too hot.
Travel tips: It’s free to visit, but there is a fee for the lavender train tour. There is plenty of free parking and a small gift shop with a wide variety of lavender themed gifts and drinks. I would bring a stroller for the toddler set and wear sneakers.  Plan on 60-90 minutes for a visit that includes a train ride.

August: Climb the ropes courses at The Adventure Park, which has two Connecticut locations: Storrs (near the University of Connecticut) and Bridgeport (on the campus of the Discovery Museum and magnet school). The Bridgeport campus covers five 5 acres with 23 ziplines, almost 200 platforms and 13 trails for a variety of ages (5+) and abilities. The Glow in the Dark nighttime events are especially popular.
When to go: There are plenty of dates and times, so there isn’t as much pressure for this activity as some of the other time-sensitive events. Make sure to check the weather before you reserve, and try for a nighttime spot for a unique way to experience the courses ( everything glows!).
Travel tips: Dress properly so that you’re comfortable and safe; wear sneakers; use the restroom before you head out on the course.

September:  Great Jack O’Lantern Blaze at Van Cortlandt Manor in New York. The displays include about 7,000 “constructed” pumpkins which are part of the annual collection and an additional 1,000 “live” pumpkins that are lit each night by thirty volunteers. Some of the most popular themes include the Pumpkin Bridge, the Statue of Liberty, the pumpkin carousel, and the Zodaic signs.
When to reserve tickets: Tickets usually go on sale the first week in September and sell out quickly. If you can go on a weeknight, you’ll have more choice of dates and smaller crowds. Crowds also tend to be smaller during the last hour of admission (9-10pm). There are fewer dates in September because the sun sets later. Over the past few years, the event has been extended through the first few weeks of November.
Travel Tips: The entire event is outdoors, so check the weather report and dress accordingly. Portapotties are available near the main entrance. A wide variety of seasonal snacks and beverages (including craft beers and wine) and a gift shop with tons of toys, apparel, and gifts is located near the entrance.
Read more about our adventures in this post

October: Cornmaze competitions are an annual event for our family. We’re lucky to have Plasko’s Farm and Jones Family Farms in Connecticut close by, but there are dozens of options throughout Connecticut, Rhode Island, and New York.  There is a good list of Connecticut cornmazes here and here. Bonus: A lot of these spots sell homemade fall goodies like apple cider donuts and offer plenty of fall decor like pumpkins, hay, and gourds.
When to go: We usually make a morning (or later afternoon) of it and enjoy all the outdoor activities. Many mazes tend to be busiest late morning though early afternoon.
Travel tips: Wear sneakers and use the restrooms at home before heading out (most farms only have portapotties). If you dress your family for photo opts, most farms provide idyllic settings for holiday card backgrounds.

December: Another one of our most cherished traditions is riding the North Pole Express to visit Santa, Mrs. Claus, and the elves. Each year, the North Pole Express leaves the Essex Steam Train depot and heads for the North Pole. Each train car has its own elf who leads guests in a singalong, a dance party, trivia games, and more! Guests elves stop by with hot cocoa and cookies, and once the train arrives at the North Pole, Santa and Mrs. Claus board the train and visit with every guest.
When to reserve tickets: Tickets usually go on sale the first week in September and sell out within minutes. Whole cars (64 seats) go on sale first and then individual tickets go on sale the following day.
Travel tips: Guests (including adults) are encouraged to wear pajamas. Bring a disposable drink holder that coffee shops offer with take out- it will make it easier (and you’ll avoid spills!) to sit the hot cocoa down safely so you don’t have to hold the cups the whole ride. Get to the train station at least 45 minutes before your departure time to explore the indoor exhibits and photo opts and to use the restrooms (and avoid the crammed restrooms aboard the train)

Something special in New York City: There are so many annual holiday events in New York City, like the Nutcracker Ballet at Lincoln Center, the Christmas Spectacular featuring the Rockettes at Radio City Music Hall, and seeing massive trees and department store windows throughout the city. You can read about 10 things we have done in New York City during the holidays here
When to reserve tickets: We usually book tickets for a holiday themed activity in New York City during the summer (early August) and plan on visiting the tree, or other popular free spots, early in the morning before large crowds.
Travel tips: Wear comfortable shoes and gloves to stay warm and keep germs at bay. Bring snacks to ward off “hangriness.” Check out some of our other travel tips here

For more fun in Connecticut (which we’ve featured in many of these activities, check out our Top 30 favorite spots in this post

And follow along on our adventures on Instagram, Twitter, Facebook, and Pinterest

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3 Comments

  1. Love them all and have treasured memories of so many.Thank you for reminding me of how special these activities are for adults and children alike!

  2. Love them all and have treasured memories of so many.Thank you for reminding me of how special these activities are for adults and children alike!

  3. Love them all and have treasured memories of so many.Thank you for reminding me of how special these activities are for adults and children alike!

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