Fall has fully arrived at Westport’s Downtown waterfront.
Pigeons gather along the waterfront in Westport, Connecticut.
Westport, CT
51 pictures
Westport in the 2026
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Janet & Arnold Bernhard Westport Library
The Janet & Arnold Bernhard Westport Library welcomes visitors in Westport, Connecticut.
Waterfront memorial walkway
A brick memorial walkway follows the waterfront in Westport, Connecticut.
Westport Farmers' Market
Vendors and shoppers gather among the stalls at the Westport Farmers' Market in Westport, Connecticut.
Levitt Pavilion for the Performing Arts
The Levitt Pavilion for the Performing Arts in Westport, Connecticut, features an outdoor performance stage beneath a tensile canopy.
Wooded waterway and footbridge
A wooded waterway opens onto a broad body of water beyond a wooden footbridge in Westport, Connecticut.
Westport waterfront
A waterfront view in Westport, Connecticut, shows calm water, shoreline buildings, trees and a paved riverside walkway.
Westport Farmers' Market
Westport Farmers' Market brings vendors and shoppers together beneath a row of tents in Westport, Connecticut.
Westport farmers market
Vendors and shoppers gather beneath tents at a farmers market in Westport, Connecticut.
Farmers market
Shoppers browse vendor stands at a farmers market in Westport.
Waterfront park by the library
A landscaped waterfront park in front of the library in Westport, Connecticut, features benches, paved walkways, ornamental lamps, trees, and a brick building.
Westport waterfront
A view across the water toward the waterfront in Westport, Connecticut.
League of Women Voters commemorative plaque
A commemorative brick walkway along the waterfront in Westport includes a 1999 plaque marking the League of Women Voters' 50 years of service to the town.
Downtown Westport View West over the Ruth Steinkraus Cohen Bridge.
A downtown Westport intersection and bridge under clear autumn skies.
Sunset+Sunfish
A sunfish rests on a pebbly shoreline as the sun sets over the water.
Compo Beach
People sit on benches and stand beneath trees beside a sandy beach.
People with a small sailboat on the beach
Three people stand beside a small sailboat on a beach as sunlight reflects off the water.
Compo beach and Cockenoe Island
Visitors relax on a sandy beach overlooking calm water and a small offshore island.
Tree-lined street in Westport
Vehicles travel along a tree-lined street in Westport, Connecticut.
Downtown Westport streetscape
Cars pass storefronts and string lights in downtown Westport, Connecticut.
Main Street in Westport
This is the top of Main Street in Westport
Westport Museum for History and Culture
The Westport Museum for History and Culture in Westport, Connecticut.
Westport Town Hall
A yellow building stands behind trees and a lawn bordered by a stone wall.
Eyeglasses.com storefront
The Eyeglasses.com storefront in Westport, Connecticut.
Westport street scene
Parked cars line a street beside a building under construction in Westport, Connecticut.
Westport Museum for History & Culture
The Westport Museum for History & Culture in Westport, Connecticut.
Eyeglasses.com storefront
The Eyeglasses.com storefront in Westport, Connecticut, with a pickup truck parked outside.
Modern residential building
A modern multi-unit residential building stands behind a field of tall vegetation and reeds.
Westport Town Hall
Westport Town Hall.
Main Street Westport
A wet downtown street lined with utility poles, storefronts and older homes under an overcast sky.
Waterfront buildings on the Saugatuck River
A waterfront view shows buildings along the opposite shore beneath an overcast sky.
Main Street westport looking north
Main Street westport looking north
eyeglasses.com storefront
The eyeglasses.com storefront is shown beside a parking area.
Post Road
Looking up the post road at the corner of main street. A rainy downtown intersection with brick sidewalks, historic storefronts, and pedestrians.
Westport ct main street
A downtown commercial street lined with shops and parked cars.
Waterfront view of the Saugatuck River
A waterfront view shows calm water, shoreline buildings and wooded hills beneath an overcast sky.
Main street westport
A decorated downtown street lined with shops, restaurants and historic buildings on an overcast day.
Main street westport
A brick-lined downtown street with storefronts, parked cars and decorative streetlights.
Saugatuck River and the Parker Harding Esplanade
A bridge crosses a canal beside red-brick industrial buildings under a cloudy sky.
Saugutuck River and the Post Road Bridge
A waterfront walkway and bridge overlook the water and brick buildings under an overcast sky.
Waterside reeds
Reeds grow along the edge of a body of water, with a modern building and wooded shoreline in the background.
Wooden footbridge closed to pedestrians
A wooden footbridge crosses a stream through tall grasses, with a warning sign restricting access.
Main Street Westport
A brick-paved downtown sidewalk features decorative streetlamps, hanging flower baskets and string lights alongside a tree-lined street.
Waterfront buildings on the Saugatuck River
Waterfront buildings line the opposite shore under an overcast sky.
Joe’s Pizza storefront construction
Construction work is underway outside Joe’s Pizza and neighboring storefronts.
Westport Library
A parking lot and brick building of the Library are shown on a rainy day.
Waterfront walkway
A waterfront walkway follows the edge of a tree-lined body of water beside a road on an overcast day.
Waterfront buildings on the Saugatuck
A waterfront view of commercial and residential buildings across the water under an overcast sky.
Saugatuck river and the Post Road Bridge
A waterfront view shows calm water and a row of commercial and residential buildings beneath an overcast sky.
Lobster cooking and cracking equipment
Setup before the Westport Rotary Lobsterfest event, gear for cooking and cracking lobsters