I’m a self-described Summer Girl for sure, so when the weather starts turning here in Connecticut I make sure to have lots on the calendar to look forward to! Planning bonding excursions and adventures really feed us as a family and help us create so many fun memories. Whenever we’re chilly indoors, or bundled up on the shorter and shorter days of the year, it’s nice to have something fun on the horizon to get excited about! I’m a bit of an over-planner if I’m being honest, so in the last 8 years of living in Connecticut (wow, it’s kind of wild to see 8 years written out like that!) we’ve tried SO many different things and discovered lots of favorites. Some of them have even become annual traditions!

Since many of you who read this blog live in the general vicinity or may be planning trips to the area, I figured I’d give you guys a little rundown of all the fun plans we have scheduled so far from now until March. Maybe it’ll offer some inspiration for your own adventures! I’d also love to know if you have any local or semi-local recommendations that you’d like to share for the Fall and Winter months. I’m always looking for new things to try out.

Jones Family Farm & Vineyard

We pick berries here in the summer, and apples in the Fall! Plus they have the most beautiful winery on site that makes for a beautiful weekend experience with or without kids.

The Pumpkin Blaze

This has been a family favorite for years! I’m always amazed by the thousands and thousands of carved pumpkins made into breathtaking sculptures. It’s just spooky enough for kids of all ages. Yummy food and drink stands are on site, too!

Hopkins Vineyard

A bit farther afield is the gorgeous Hopkins Vineyard! The wines are delicious and they have weekend live music that is fun for all ages. An absolutely gorgeous setting.

Great Wolf Lodge

We are bringing the kids to Great Wolf Lodge (an indoor water park resort) this fall for a day of splashy fun! My kids love the mystical scavenger hunt the hotel offers, and this fall they have Howl-oween events for the month of October– with spooky activities and a monster mash dance party!

Glow Wild Lantern Festival at Beardsley Zoo

We love the zoo, and this festival has glowing lantern installations after dark with lots to see and explore. It’s a great family activity for all ages

Major’s Birthday!

Major turns 8 next month, and he is celebrating with an Escape Room experience with a few of his buddies! I’ll share more about that next month, depending on if we end up liking the place. I’m excited to try out an Escape Room for the first time.

Ballet Season

Our Ballet Date Nights start again this Fall! I highly recommend trying out a performance for a date idea if you’ve never been. It’s so romantic and fancy in the best way, and we always have a blast.

Yale Art Gallery

One of our favorite cold or crummy weather activities is the Yale Art Gallery in New Haven. It’s such a great museum filled with art from all eras, and the museum is totally free! We usually grab pizza after when we go with the kids.

The Nutcracker at Lincoln Center

I’m continuing my annual tradition with Major and taking him on a 1:1 date to watch the Nutcracker this Fall! It gets more and more fun each year. This year I splurged on particularly good seats, so I’m excited to surprise him!

Major Dancing In The Nutcracker

Major’s dance school puts on a very professional weekend of performances each holiday season of The Nutcracker, and this year he has been cast as a Blue Soldier and Coffee Attendant. I can’t wait to watch him up on stage again!

Hosting Thanksgiving

We had such a wonderful time hosting Thanksgiving at our home last year that I think we will do it again this year! There is nothing that makes me happier than creating memories in our home with loved ones, and Thanksgiving is one of our favorite holidays.

“Annie” at Madison Square Garden

Our big Christmas gift for the kids this year is tickets to see Annie at MSG Theater! I know they are going to FLIP OUT. Whoopie Goldberg is even playing Miss Hannigan the week we’ll be there, which will be so cool to see.

Radio City Christmas Spectacular

One of my favorite holiday traditions is going to see the Radio City Rockettes! This is such a fun show for all ages and a special family outing. We have only missed one year in the last 15! They have been updating the show with new technology the past few years and last year the number with the drones was especially cool and unique.

Holiday High Tea at The Plaza

I’ve been trying to organize a girls’ holiday experience for Tea at the Plaza Hotel for the last few years, but this year is the year! I’m so excited to get all dressed up with my girlfriends to sip tea and champagne and toast to the season. For those of you visiting the city with little ones, I did the Eloise Tea at the Plaza with Marlowe when she was five and it was an incredible experience. Highly recommend it for a special treat!

Stowe, VT for February Break

For our vacation with the kids this year, we are going to Stowe for some Winter Wonderland fun! I’ve heard amazing things about Stowe and how family-friendly it is, but I never really knew where to stay or how to book a trip there in a way that made sense for our needs as a family. I recently found the best home rental site, Mountain View Vacations, which has gorgeous properties in the area and beyond. I especially love that it’s run by a family with kids, and they really know what families want and need. I’ll share the exact house we rented after we leave, but I’m DYING over it. So beautiful!

Mateo turns 5

I can’t believe Mateo is turning 5 in March! We’re going to have a birthday party for him, and we are leaning towards an animal theme. Stay tuned!

I turn 40

Gah! I’m thinking about going to London with Ian and the kids to celebrate. We had so much fun there last time we went, and we’ll have family in the area around my birthday so it could all work out perfectly. Stay tuned as more plans develop, but I’m really looking forward to this major milestone!

Photographs by Julia Dags | Copyright © 2024 Happily Eva After, Inc. All Rights Reserved.

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