Labor Day Events In CT: Secrets To Planning A Great Weekend | Stanton House Inn

flag in the grassLabor Day weekend is just around the corner. And with it comes the opportunity to bid farewell to summer with a memorable weekend getaway. You’ll find plenty of exciting Labor Day events in CT and activities across the state that cater to all tastes.


From exhilarating amusement parks to serene state parks, there’s something for everyone in the Nutmeg State.


So why not make this Labor Day weekend one to remember in Connecticut?

But first: Labor Day weekend in Fairfield County

We already have a full guide to exploring our corner of Connecticut over the three day weekend.


With special events like St Leo’s Fair in Stamford and clambakes on Sheffield Island, there’s plenty more to checkout.


And all without driving all over the state.


Quick hits

  • Celebrate Labor Day in style with family-friendly events across Connecticut.
  • Enjoy activities, music & food from the past at Mystic Seaport Museum or explore nature parks and beaches for outdoor adventures!
  • Spend quality time together attending concerts, painting lessons or amusement park rides, perfect destination for a fun weekend getaway!


Celebrate Labor Day in Style: Top Connecticut Events

People having fun at a Labor Day weekend event in Connecticut

Connecticut knows how to celebrate the unofficial end of summer in style. There’s an array of vibrant festivals and Labor Day weekend events across CT for you and your friends.


With so many events happening across the state, it’s the perfect opportunity to plan Labor Day weekend getaways and make lasting memories. Whether you’re:

  • A history buff
  • A foodie
  • Or just looking to enjoy some live music


Some corner of Connecticut has you covered this weekend.


Each unique event offers something special. So you’re sure to have an unforgettable Labor Day weekend.

Mystic Seaport Museum Labor Day Celebration

The Mystic Seaport Museum Labor Day Celebration is a fantastic event for a touch of history, culture, and hands-on fun. Special programming runs from Saturday, September 3 to Monday, September 5. During this family-friendly event, A Spectacle in Motion: The Grand Panorama of a Whaling Voyage ‘Round the World, a 1275-foot-long painting, will come to life for you. The panorama recounts the fascinating journey of a typical New Bedford whale ship in the middle of the nineteenth century. The story follows along as it traveled “round the world” in search of whales. You’ll experience diverse cultures, food, and the music of a bygone era.


Indulge your senses with delicious food trucks and live music. All while embracing your inner explorer through a range of hands-on activities. It doesn’t matter if you’re a history enthusiast or simply looking for unique Labor Day weekend getaways. The Mystic Seaport Museum Labor Day Celebration is not to be missed.


If you’d rather avoid the Labor Day crowds at Mystic, CT, then be sure to read our guide to cute towns across the state. Any of them would be perfect for a CT day trip.

New England’s Old England Renaissance Faire

Step back in time and immerse yourself in the world of the Old England Renaissance Faire. Held over Labor Day weekend, this enchanting event offers a delightful escape. From fantasy writers meet-and-greets and costume contests, to:

  • Jousting
  • Juggling
  • And archery demonstrations


There’s no shortage of excitement here.


The Faire also boasts a bustling bazaar, knights school, and captivating falconry shows. So why not make the most of your three-day weekend and embark on a thrilling journey to the past at New England’s Old England Renaissance Faire?

Woodstock Fair Extravaganza

An image of the lively crowd enjoying Labor Day events in CT at the Woodstock Fair Extravaganza.


As summer draws to a close, the Woodstock Fair Extravaganza provides the perfect last hurrah. This lively Labor Day weekend event in the town of Woodstock, CT, features:

  • Roller coasters
  • Live music
  • Tractor pulls
  • And much more


For a touch of nostalgia, be sure to explore the fair’s antique exhibits and crafts. They offer a charming insight into days gone by.


With an array of fun-filled activities, the Woodstock Fair Extravaganza caters to all ages. So gather your loved ones and head to this unforgettable event.

Blues, Views & BBQ Festival in Westport

For a feast of music, food, and fun, look no further than the Blues, Views & BBQ Festival in the town of Westport, Connecticut. This lively event showcases a mix of up-and-coming and local talent alongside headliners. You’ll discover two stages of music, mouthwatering barbecue, and food trucks to satisfy your cravings.


In addition to the fantastic live music, kids can enjoy bounce houses and a range of other activities. So why not make the most of your Labor Day weekend and head to Westport for a taste of blues, views, and delicious barbecue?


Be sure to read our guides to:

For even more fun recommendations.

Outdoor Adventures for the Long Weekend

People hiking at Flander's Land Trust Whittemore Sanctuary in Connecticut

Do you prefer to spend your Labor Day weekend exploring the great outdoors? Connecticut has plenty to offer. With the beautiful scenery and mild weather, it’s the perfect time to get outside and appreciate nature’s wonders.


Connecticut’s state parks provide a wealth of opportunities for exploration and relaxation. And that goes whether you’re an adrenaline junkie or simply seeking a tranquil retreat. So why not take advantage of the Federal holiday and embark on a thrilling outdoor adventure?

Hiking at Flander’s Land Trust Whittemore Sanctuary

Silver Sands State Park in Connecticut


Nestled in Woodbury, CT, the Flander’s Land Trust Whittemore Sanctuary is a nature lover’s paradise. This pristine preserve offers a range of picturesque hiking trails, as well as a fascinating nature center to explore.


With its lush landscapes and abundant wildlife, the sanctuary is the perfect setting for a weekend hike. Immerse yourself in the natural beauty and breathe in the fresh air. Let the tranquility of the sanctuary wash over you as you reconnect with nature.


And be sure to read our full guide to hiking trails across Connecticut, for more day trip ideas.

Relaxing at Silver Sands State Park

People exploring Bolton Notch State Park in Connecticut

If a laid-back beach experience is more your style, Silver Sands State Park is the ideal pick from the list of the best things to do in Milford, CT. The park features a scenic boardwalk, rocky beaches, and opportunities for saltwater swimming and fishing.


Take a leisurely stroll along the stunning shoreline. Or simply relax on the beach and soak up the sun. Captivating views and serene atmosphere make Silver Sands State Park a blissful retreat from the hustle and bustle of daily life. It’s perfect for Labor Day weekend getaways.

There are plenty more Connecticut beaches to checkout over the long weekend, depending on where you’ll be.

Exploring Bolton Notch State Park

Family having fun at Quassy Amusement Park and Sandy Beach Club in Connecticut

For a true taste of Connecticut’s natural beauty, plan a trip to Bolton Notch State Park. This public recreation area offers a variety of activities. Outdoor activities range from fishing and picnicking to bird watching and hiking along the park’s 20.2-mile trail.


Whether you’re seeking adventure or a peaceful escape, Bolton Notch State Park delivers. Spend the day immersed in nature. The park’s picturesque surroundings provide a perfect backdrop for a memorable Labor Day weekend.

Even more outdoor activities across Connecticut

Labor Day weekend is all about enjoying the outdoors one last time.


So a few more fun options for things to do outdoors all over Connecticut include:

Family Fun on Labor Day Weekend

Labor Day weekend is the perfect time to reconnect with family and enjoy some quality time together. Connecticut offers a wealth of family-friendly activities, from:

  • Thrilling amusement parks
  • To inspiring art exhibits
  • And state park adventures

With so much to see and do, you and your kids will be spoilt for choice.

Quassy Amusement Park and Sandy Beach Club

Are thrills and excitement what you seek? Quassy Amusement Park and Sandy Beach Club have you covered. With over 20 rides and attractions, this popular destination offers hours of fun for the whole family.

In addition to the amusement park, visitors can enjoy swimming and wading in the sparkling water, as well as team-building activities such as sand volleyball and horseshoes. With so much to see and do, Quassy Amusement Park and Sandy Beach Club promise a fantastic day out for all ages.

American Impressionist Painting Exhibit and Lessons in Old Lyme

For a more artistic experience, consider a visit to the American Impressionist Painting Exhibit and Lessons in Old Lyme, Connecticut. This captivating exhibition showcases the unique appeal of Connecticut for American Impressionist artists and offers painting lessons for budding artists of all ages.


From viewing masterpieces to trying your hand at painting, this engaging place provides a fascinating insight into the world of American Impressionism. Other Connecticut museums to explore American Impressionism include: the Greenwich Historical Society and the Weir Farm National Historic Site.

Rocky Neck State Park Activities

Rocky Neck State Park offers a variety of summer activities to suit all tastes. From saltwater fishing and swimming to hiking and picnicking, there’s plenty to do at this picturesque park.


With its half-mile crescent beach, boardwalk, and bathhouses, Rocky Neck State Park is the perfect setting for a fun-filled day out with the whole family.

Labor Day Weekend Concerts and Performances

People enjoying a Labor Day weekend concert at Walnut Beach in Connecticut

If live music is more your scene, Connecticut offers plenty of opportunities to enjoy summer concerts and performances during the Labor Day weekend. There’s no shortage of entertainment to suit all tastes.


So whether you’re a fan of blues, jazz, or rock, be sure to check out one of these fantastic concerts and performances. With a variety of genres and venues to choose from, you’ll be sure to find the perfect soundtrack to your three days of celebrations.

Milford’s Free Concert Series at Walnut Beach

People listening to live music at Durham Central Park in Connecticut


For a beach-themed musical experience, head to Milford’s Free Concert Series at Walnut Beach. This annual summer series features a variety of live music events. They take place every Sunday from July through Labor Day at the Rotary Pavilion. Bring your chairs, blankets, and a picnic. And don’t forget your dancing shoes! With an array of bands and genres to choose from, this lively event promises a fun-filled evening.

Live Music at Durham Central Park

For a more diverse musical offering, consider the live music events at Durham Central Park. This free concert series, known as PLAYlist, is presented by Durham Central Park and WNCU 90.7FM. It takes place on the first Friday of the month from May to October.


Featuring a range of genres from jazz to hip-hop, the concerts are sure to delight music enthusiasts of all ages. And a big dance party rounds off the evening.

Enjoy the last hurrah of Summer, or get ready for Fall in CT

Labor day weekend, and September in general, is the in-between period.


It’s still warm enough to enjoy so many summer activities in CT. And yet it’s the beginning of fall in Connecticut, as well.


So, keep reading based on whether you want to keep enjoying the summer, or if you’re ready for the autumnal season. Some of our most popular guides this time of year include:

And be sure to read our full guide to the most unique attractions, activities, and things to do in Connecticut.


We hope you rediscover your love of Connecticut!

Frequently Asked Questions

What is there to do in Connecticut on Labor Day weekend?

If you’re looking for a fun Labor Day weekend in Connecticut, check out:

  • The Woodstock Fair
  • Goshen Fair
  • Market Weekend at The Annual Connecticut Renaissance Faire in Lebanon
  • And the Annual Mark Twain Library Book Fair in Newtown


What is a historical event that happened in Connecticut?

Connecticut has a long and rich history. Some major events include:

  • The founding of the colony by Thomas Hooker in 1636
  • The establishment of Yale University in 1701
  • And the Hartford Convention in 1814

What is there to do in Connecticut on Labor Day weekend?

This Labor Day weekend, you can enjoy some outdoor fun in Connecticut with activities like camping, fishing, and hiking. Plus, if you’re looking to do some shopping, you can find plenty of outdoor markets and farmers markets all around the state.


Finally, Connecticut has lots of great parks that are perfect for taking a leisurely stroll or cycling. Enjoy your long weekend!

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