Destination Westport: In Gatsby’s Shoes

October 10, 2026 10:00am to 11:30 am

September 4 @ 5:13 am

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. 

$20 for Museum members

Generously Sponsored By:

Pickle Me This! Learn to make pickles like its 1776

Ages 8 and up

Family Friendly

ou know pickles from the supermarket, but did you know you can easily make your own? Pickling is a historic way of preserving food to keep it from spoiling. Throughout history, cooks rich and poor pickled vegetables and fruit to have food all year long. Quick refrigerator pickles use only vinegar, sugar, salt, and your favorite flavorings.  They don’t require a lot of ingredients or complicated know-how and can be kept in the refrigerator for your next picnic!  

Learn how to make quick refrigerator pickles using just a few simple ingredients. Discover some of the history and the science behind pickling and take home a jar you have made. You will even be able to create your own logo to put on your jar. All materials supplied by the Museum.  

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. 

August 7 2pm to 3pm

$15 covers event only, museum admission additional

Nell Dorr: Only Beauty Remains

Context Matters 

Social events do not occur in a vacuum nor should they be interpreted as such. To try and understand a person of historical import, we must first explore the time in which they lived and the situations that shaped them. In order to provide historical context this exhibit is produced in “layers”.

The catalogue offers greater detail about Nell Dorr’s life and work and the online exhibition shares details about the world in which the photographer lived and how events may have influenced or shaped her artistic view. In each section of the exhibit and throughout the catalogue, you will find a QR code that will allow you to learn more. 

The online exhibit is a compliment to the full exhibition at the museum. All of the materials here are exclusive to the online version. Select a topic area to see associated objects, explore resources and learn about Nell Dorr.

Explore resources and other readings to get a better understanding of the world Dorr was apart of.

Green’s Farms Church & the West Parish of Fairfield, 1711-1736

The establishment of the Congregational Church of America dates back to the founding of this nation with the arrival of religious dissenters from England to Massachusetts Bay Colony in 1620. Called Puritans in England — a derogatory term referring to their zeal for simplicity in church organization and worship — they believed each church should be organized with members who enter a covenant agreement and had the right to choose their own minister.

In the 1630s and 1640s, thousands of Puritans arrived in New England and flourished with the conviction that they were chosen by God to play a central role in the unfolding of this new land and human history at large. As such, churches and church leaders played an important role in shaping New England society. The organizational system of Congregational churches required mutual trust and personal commitment, yet this was not always a given. Voting in Massachusetts was limited to individuals who had been formally admitted to the church after a detailed interrogation of their religious views and experiences. Thomas Hooker disagreed with the limitation of suffrage in the Massachusetts Colony and in 1636, led one hundred followers to found Hartford. After 1636, freeman (eligible voter) settlements were formed throughout Connecticut.

In 1639, Roger Ludlowe and a group of settlers from Windsor came to modern day Fairfield and formed The First Church of Fairfield. By 1644, Fairfield was the fourth largest town among the colony’s nine towns and extended from Stratford to Norwalk. As populations grew and church attendance was mandatory, groups began campaigning for the right to establish their own parishes.  In 1708, the Bankside farmers, Thomas Newton, John Green, Henry Gray, Daniel Frost and Francis Andrews started their petition to form the West Parish of Fairfield, which is the modern day Green’s Farm Church in Westport.

Dive in and learn more about the history of Westport, the quintessential New England town

Bankside Farmers, 1648-1711

When Connecticut was a British colony, the area east of the Saugatuck River to the border of Fairfield and west of the Mill River was known as Green’s Farms. Thomas Newton, John Green and Henry Gray were given a land grant to settle the area in 1648 with Daniel Frost and Francis Andrews joining them within a few years. The group later became known as the Bankside Farmers. In subsequent generations, others like Joshua Jennings possessed landholdings encompassing a large parcel of Green’s Farms. 

Settlers cultivated the rich soil of Greens Farms initially for their own subsistence and later for commercial profit. Positioned on the Long Island Sound, Green’s Farms was also a seafaring community which tapped into the export trade. Flax was grown for linen, and corn–also known by the Native name maize–was grown for the settlers’ families, their cattle, and for export to the Caribbean where it was used to feed enslaved people. 

Food was also harvested from the sea and fish, clams, and oysters were part of the bounty. Fish and lobsters were so plentiful they were also used for fertilizer. 

Dive in and learn more about the history of Westport, the quintessential New England town