Destination Westport: In Gatsby’s Shoes
2025-05-31 09:30 - 11:00 (America/New_York) | Longshore Mariana, 260 Compo Rd S, Westport, Connecticut, 06880, United States
Step Into the Roaring Twenties: Fitzgerald’s Summer in Westport – A Tour Like No Other!

Picture this: It’s the summer of 1920, and Westport, a quiet farm town, becomes the summer escape for one of New York’s most glamorous couples—F. Scott and Zelda Fitzgerald. Seeking a breath of fresh air from their whirlwind Jazz Age lifestyle, the Fitzgeralds retreat to a charming 18th-century farmhouse, a silent witness to revolution and the birth of a nation.

In this idyllic setting, Zelda swims in the sparkling waters of the Long Island Sound, while Scott, inspired by the calm, works furiously on what would become his magnum opus—The Great Gatsby. The magic of this summer shaped his legendary novel, and now you have the chance to walk in the very footsteps that inspired one of the greatest American tales ever told.

Join us for a lively and immersive 90-minute tour through the stunning landscapes that once captivated the Fitzgeralds. As you stroll through the picturesque sites that influenced Scott’s writing, you’ll step back in time to a world of flappers, jazz, and literary genius. This isn’t just a tour—it’s a journey into the heart of the Jazz Age.

Be prepared for a vigorous, yet stunning walk through one of the East Coast’s most enchanting settings. Don’t forget to bring water and wear your most comfortable shoes for this unforgettable, Gatsby-esque adventure.

PARKING INFORMATION: Guests should park at Longshore Marina, in Lot F, along the asphalt and dirt areas.

Tickets are $20 for members and $25 for nonmembers. Reservations are required, so be sure to secure your spot today! Space is limited to just 25 lucky guests per tour. Additional tours may be added if demand is high. If the tour sells out or you’re interested in a private tour, simply email programming@westporthistory.org.

Tickets are nonrefundable. If you need to cancel, your ticket will be considered a donation, and we will gladly issue you a donation receipt.

Don’t miss your chance to immerse yourself in the glamour and excitement of the Jazz Age! Register today and experience the magic of the Fitzgeralds’ Westport.

Westport Museum is accessible via public transit! The Westport-Saugatuck railroad station has connections on the MTA New Haven line from Norwalk, Bridgeport, Stratford, Milford, and New Haven, and more. Uber 2.3 miles to the Museum or take the Norwalk Wheels bus transit system when available to Post Road West at Myrtle Avenue, which is a brief 7-minute walk from the Museum!

Park on Myrtle Avenue and Avery Place or behind Westport Town Hall or in the Baldwin Parking lot. Westport Museum is a privately funded 501(c)3 museum not affiliated with or managed by Westport Town government. Please support our work by donating here.

Generously Sponsored By:

Freedom’s Journey: Connecting Westport to Juneteenth’s Legacy
2025-06-18 18:00 - 20:30 | Westport Library, 20 Jesup Road, Westport, Connecticut, 06880, United States
Reception at 6:30 pm; Program begins at 7pm

Join Executive Director of Westport Museum for History and Culture Ramin Ganeshram as she shares the hidden history of Westport’s connection to Juneteenth, the national holiday celebrating the final liberation of enslaved people during America’s Civil War. Based on the Museum’s extensive research into the Union Army and Black History in the region, this event will share some surprising unknown facts about Westport’s role in the fights for freedom — as well as genuine Civil War artifacts from the Museum’s collection.

You can register on the Library’s website here!

Destination Westport: Paths of Patriots
2025-06-08 10:00 - 11:00 | Greens Farm Lower Cemetery, Nyala Farms Rd, Westport, Connecticut, 06880, United States
Discover the Heroes of 1779 and Beyond during our Paths of Patriots Walking Tour!

On July 8, 1779, Green’s Farms became a battleground in the fight for freedom, as British soldiers attacked and burned buildings to the ground. Step into the past and uncover the untold stories of Westport’s role in the American Revolution. As you stroll through a historic cemetery, you’ll pay tribute to the brave men and women who served in the war for independence.

Hear the gripping tale of that fateful day when Green’s Farms burned, discover the stories of enslaved Africans who, against all odds, fought for their freedom, choosing sides in the hope of having their voices heard in the battle for liberty.

This is not just a walk through history—it’s a vivid journey through the sacrifices and struggles that shaped our nation. Experience Westport’s place in the Revolution in a way you never have before.

Park on Nyala Farms Road and meet us at the marked green at the back entrance to the cemetery. The terrain is uneven, and with the possibility of warm weather, we recommend wearing comfortable walking shoes and bringing bottled water.

Tickets are $10 for members and $15 for nonmembers, and pre-registration is required. Space is limited to just 25 participants per tour, so don’t wait! If demand is high, additional tours may be added. Should the tour sell out or if you’re interested in a private tour, please contact us at programming@westporthistory.org.

Please note, tickets are nonrefundable. If you need to cancel, your ticket will be considered a donation, and we’ll be happy to issue you a receipt for your generous contribution.

Join us for a compelling, immersive experience into Westport’s Revolutionary history—register today!

Easily accessible via public transit—if you make it back! The Westport-Saugatuck railroad station has connections on the MTA New Haven line from Norwalk, Bridgeport, Stratford, Milford, and New Haven, and more. Uber 2.3 miles to the Museum or take the Norwalk Wheels bus transit system when available to Post Road West at Myrtle Avenue, which is a brief 7-minute walk from the Museum!

Park on Myrtle Avenue and Avery Place or behind Westport Town Hall or in the Baldwin Parking lot. Westport Museum is a privately funded 501(c)3 museum not affiliated with or managed by Westport Town government. Please support our work by donating here.

Generously Sponsored By:

Destination Westport: Saugatuck Stories
2025-07-12 10:00 - 11:00 | Saugatuck Train Station, 1 Railroad Pl, Westport, Connecticut, 06880, United States
Explore the Hidden Stories of Saugatuck!

Join us for a fascinating one-mile walking tour through Saugatuck, located at the mouth of the Saugatuck River and Long Island Sound. Discover the area’s rich history, from pre-colonial times to the early 20th century, including stories of commerce, the Atlantic trade, and the immigrant and women’s experiences that shaped the town.

Meet us at the Saugatuck Train Station (New York-bound side, 45 Railroad Place). Tickets are $10 for members and $15 for non-members. Space is limited to 25 people per tour, so reserve your spot today! If the tour is sold out or you’re interested in a private tour, email programs@westporthistory.org.

Reservations are required, and tickets are nonrefundable, though we will issue a donation receipt if you need to cancel. Additional tours may be added based on demand. Don’t miss this unique opportunity to explore Saugatuck’s history!

Westport Museum is accessible via public transit!! The Westport-Saugatuck railroad station has connections on the MTA New Haven line from Norwalk, Bridgeport, Stratford, Milford, and New Haven, and more. Uber 2.3 miles to the Museum or take the Norwalk Wheels bus transit system when available to Post Road West at Myrtle Avenue, which is a brief 7-minute walk from the Museum!

Park on Myrtle Avenue and Avery Place or behind Westport Town Hall or in the Baldwin Parking lot. Westport Museum is a privately funded 501(c)3 museum not affiliated with or managed by Westport Town government. Please support our work by donating here.

Generously Sponsored By:

Juneteenth: Black History Walking Tours
2026-06-19 10:00 - 16:00 | Westport Museum for History & Culture, 25 Avery Place, Westport, CT, 06880, United States
Free tours for Juneteenth!

FREE EVENT

Explore Westport’s Hidden African American History

Step back in time and discover the powerful, untold stories of Westport’s African American community! Join us for a guided walking tour through downtown Westport, based on the Museum’s award-winning exhibit Remembered: The History of African Americans in Westport. Three tours will be offered at 10:00 am and 4:00 pm thanks to the generous support of TEAM Westport.

Westport Museum’s Staff will share the stories of soldiers, sailors, activists, artists, and respected citizens whose legacies are woven into the fabric of this town. Visit historic sites and buildings, some still standing, others long gone. Explore this rich history firsthand and follow along with our Remembered virtual exhibit available online.

The tour will meet at the Westport Museum’s brick walk along Myrtle Avenue. Expect 1-2 miles of sidewalk walking, so please bring water and wear suitable outdoor attire. Reservations are required, and space is limited to just 20 participants per tour. Don’t miss your chance — register online today before they fill up.

Take this opportunity to celebrate history, culture, and community — sign up now!

Westport Museum is accessible via public transit! The Westport-Saugatuck railroad station has connections on the MTA New Haven line from Norwalk, Bridgeport, Stratford, Milford, and New Haven, and more. Uber 2.3 miles to the Museum or take the Norwalk Wheels bus transit system when available to Post Road West at Myrtle Avenue, which is a brief 7-minute walk from the Museum!

Park on Myrtle Avenue and Avery Place or behind Westport Town Hall or in the Baldwin Parking lot. Westport Museum is a privately funded 501(c)3 museum not affiliated with or managed by Westport Town government. Please support our work by donating here.

Generously Sponsored By:

Destination Westport: Westport Sanitarium
2025-10-11 10:00 - 11:00 | Winslow Dog Park, 25 CT-136, Westport, Connecticut, 06880, United States
This Halloween season, dare to uncover the chilling past of Westport’s lost sanitariums, where heartbreak, psychological control, and eerie medical practices once thrived. Though the buildings have vanished, the spirits remain—haunting the grounds of Winslow Park.

Join us for a spine-tingling tour through this historic site, where you’ll hear real stories of the doctors, administrators, and patients who once walked these halls. As you explore, you’ll see haunting images and uncover secrets that linger in the shadows—tales of life, death, and the unexplained.

From the unsettling reality of early mental health treatments to the restless souls who may still roam, this is your chance to experience the darker side of Westport’s history. Are you brave enough to step into the past?

Meet us at the cement path in front of the parking lot along Compo Road North. We recommend wearing comfortable walking shoes and bringing bottled water, as the ground is uneven and the weather may be warm. Be prepared for a chilling, unforgettable adventure.

Tickets are $10 for members and $15 for nonmembers, with reservations required. Space is limited to just 25 participants, so be sure to secure your spot before it’s too late! If the tour sells out or you’d like to arrange a private tour, email us at programs@westporthistory.org. Tickets are nonrefundable, but if you need to cancel, your purchase will be considered a donation, and we’ll gladly issue you a donation receipt.

This Halloween, dive into the eerie past with us. Dare to explore the darker side of history? Join us for this spooky tour and other Spooktober events—click here to explore more!

Easily accessible via public transit—if you make it back! The Westport-Saugatuck railroad station has connections on the MTA New Haven line from Norwalk, Bridgeport, Stratford, Milford, and New Haven, and more. Uber 2.3 miles to the Museum or take the Norwalk Wheels bus transit system when available to Post Road West at Myrtle Avenue, which is a brief 7-minute walk from the Museum!

Park on Myrtle Avenue and Avery Place or behind Westport Town Hall or in the Baldwin Parking lot. Westport Museum is a privately funded 501(c)3 museum not affiliated with or managed by Westport Town government. Please support our work by donating here.

Generously Sponsored By:

Destination Westport: Saugatuck Stories
2025-10-12 10:00 - 11:00 | Saugatuck Train Station, 1 Railroad Pl, Westport, Connecticut, 06880, United States
Explore the Hidden Stories of Saugatuck!

Join us for a fascinating one-mile walking tour through Saugatuck, located at the mouth of the Saugatuck River and Long Island Sound. Discover the area’s rich history, from pre-colonial times to the early 20th century, including stories of commerce, the Atlantic trade, and the immigrant and women’s experiences that shaped the town.

Meet us at the Saugatuck Train Station (New York-bound side, 45 Railroad Place). Tickets are $10 for members and $15 for non-members. Space is limited to 25 people per tour, so reserve your spot today! If the tour is sold out or you’re interested in a private tour, email programming@westporthistory.org.

Reservations are required, and tickets are nonrefundable, though we will issue a donation receipt if you need to cancel. Additional tours may be added based on demand. Don’t miss this unique opportunity to explore Saugatuck’s history!

Generously Sponsored By:

Darkness: Experience CT's Witch Panic
2025-10-16 19:00 - 20:00 | Westport Museum for History & Culture, 25 Avery Place, Westport, CT, 06880, United States
Darkness, Inside the Mind of Connecticut’s Witches is a unique Halloween experience. Enter 1647 and witness the witch trials that European colonists experienced through their own words, in the darkness that pervaded their everyday lives. Sit with us in the dark and hear about superstitions of witchcraft and the belief that danger—both physical and supernatural—was all around.

This event will discuss mature themes in complete darkness for extended periods. Our program is held inside our newly renovated historic 19th century barn. Darkness is not a haunted house, though traditionally “scary” topics will be examined. Phones and light sources are not permitted. This event is not recommended for children under 10, adult supervision is mandatory.

Tickets $10 for members, $15 for non-members. Reservations are required, register online below. Tickets are nonrefundable. In the event you must cancel, we will consider your purchase a donation and will happily issue you a donation receipt.

Join us for more Spooktober programs, exploring the darker side of history. Click here to explore more.

PopShop Market
2026-05-02 11:00 - 15:00 | Westport Museum for History & Culture, 25 Avery Place, Westport, CT, 06880, United States
Enjoy spring weather and shop local! On May 2nd the Westport Museum will be once again hosting our Popshop, featuring over 30 vendors with offerings from handmade clothing to one-of-a-kind knickknacks. Join us to support an incredible lineup of elevated small business vendors—perfect for finding thoughtful Mother’s Day gifts, something special for the girls, grads, teachers, or a little treat for yourself.

It’s the ultimate spring shopping experience in a beautiful setting—we can’t wait to see you there!

Westport Museum is accessible via public transit! The Westport-Saugatuck railroad station has connections on the MTA New Haven line from Norwalk, Bridgeport, Stratford, Milford, and New Haven, and more. Uber 2.3 miles to the Museum or take the Norwalk Wheels bus transit system when available to Post Road West at Myrtle Avenue, which is a brief 7-minute walk from the Museum!

Park on Myrtle Avenue and Avery Place or behind Westport Town Hall or in the Baldwin Parking lot. Westport Museum is a 501(c)3 museum not affiliated with or funded by the Town of Westport. Please support our work by donating here.

Destination Westport: In Gatsby’s Shoes
2026-09-26 10:00 - 11:30 | Longshore Mariana, 260 Compo Rd S, Westport, Connecticut, 06880, United States
Step Into the Roaring Twenties: Fitzgerald’s Summer in Westport – A Tour Like No Other!

Picture this: It’s the summer of 1920, and Westport, a quiet farm town, becomes the summer escape for one of New York’s most glamorous couples—F. Scott and Zelda Fitzgerald. Seeking a breath of fresh air from their whirlwind Jazz Age lifestyle, the Fitzgeralds retreat to a charming 18th-century farmhouse, a silent witness to revolution and the birth of a nation.

In this idyllic setting, Zelda swims in the sparkling waters of the Long Island Sound, while Scott, inspired by the calm, works furiously on what would become his magnum opus—The Great Gatsby. The magic of this summer shaped his legendary novel, and now you have the chance to walk in the very footsteps that inspired one of the greatest American tales ever told.

Join us for a lively and immersive 90-minute tour through the stunning landscapes that once captivated the Fitzgeralds. As you stroll through the picturesque sites that influenced Scott’s writing, you’ll step back in time to a world of flappers, jazz, and literary genius. This isn’t just a tour—it’s a journey into the heart of the Jazz Age.

Be prepared for a vigorous, yet stunning walk through one of the East Coast’s most enchanting settings. Don’t forget to bring water and wear your most comfortable shoes for this unforgettable, Gatsby-esque adventure.

PARKING INFORMATION: Guests should park in Lot F at Longshore Club Park, just past the E.R. Strait marina. Park along the asphalt and dirt areas.

Tickets are $20 for members and $25 for nonmembers. Reservations are required, so be sure to secure your spot today! Space is limited to just 25 lucky guests per tour. Additional tours may be added if demand is high. If the tour sells out or you’re interested in a private tour, simply email programming@westporthistory.org.

Tickets are nonrefundable. If you need to cancel, your ticket will be considered a donation, and we will gladly issue you a donation receipt.

Don’t miss your chance to immerse yourself in the glamour and excitement of the Jazz Age! Register today and experience the magic of the Fitzgeralds’ Westport.

Westport Museum is accessible via public transit! The Westport-Saugatuck railroad station has connections on the MTA New Haven line from Norwalk, Bridgeport, Stratford, Milford, and New Haven, and more. Uber 2.3 miles to the Museum or take the Norwalk Wheels bus transit system when available to Post Road West at Myrtle Avenue, which is a brief 7-minute walk from the Museum!

Park on Myrtle Avenue and Avery Place or behind Westport Town Hall or in the Baldwin Parking lot. Westport Museum is a privately funded 501(c)3 museum not affiliated with or managed by Westport Town government. Please support our work by donating here.

Generously Sponsored By:
