Destination Westport: In Gatsby’s Shoes

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.