Ann's Guidebook

Ann
Ann's Guidebook

Beaches

If you are in Weston for the summer, you absolutely must visit Westport's Compo Beach. It's not too far from Weston -- only 15 minutes away by car -- and totally worth it. Great for hanging out with both friends and family in the afternoon or evening. The sunsets here are gorgeous.
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Compo Beach
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If you are in Weston for the summer, you absolutely must visit Westport's Compo Beach. It's not too far from Weston -- only 15 minutes away by car -- and totally worth it. Great for hanging out with both friends and family in the afternoon or evening. The sunsets here are gorgeous.

City/town information

Westport is what you think of when you picture a New England coastal town. Some of its highlights are the vibrant downtown dotted with pedestrian accessible shops and restaurants, Compo beach, Longshore Sailing School, Sherwood Island State Park, Silverman's Farm, and so much more. At only 10 minutes away from Weston, it's a must-visit.
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Westport
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Westport is what you think of when you picture a New England coastal town. Some of its highlights are the vibrant downtown dotted with pedestrian accessible shops and restaurants, Compo beach, Longshore Sailing School, Sherwood Island State Park, Silverman's Farm, and so much more. At only 10 minutes away from Weston, it's a must-visit.
While a much larger town than Weston, Fairfield retains its quintessential New England feel through its architecture and wide array of local shops & restaurants. Only 20 minutes away, I'd recommend at least seeing it to get a feel for the area. If you weren't sold then, at least check out the wonderful pizzeria called "Colony Grill."
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Fairfield
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While a much larger town than Weston, Fairfield retains its quintessential New England feel through its architecture and wide array of local shops & restaurants. Only 20 minutes away, I'd recommend at least seeing it to get a feel for the area. If you weren't sold then, at least check out the wonderful pizzeria called "Colony Grill."

Nature

Roughly 5 minutes away from our home, Devil's Den Preserve is a spectacular hiking and adventure location, for both friends and family alike. You can trek on more than 20 miles of trails, bringing you to waterfalls and high rocky ledges. If you love birdwatching, some 140 bird species have been recorded on this land, from pileated woodpeckers to ruffed grouses. If plants are more your thing, more than 500 kinds of trees and wildflowers grow here. My favorite part has always been the lake -- there's really nothing better than it in Fairfield County. Regardless, if the outdoors are what you're looking for, here's the place to be.
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Devil's Den Preserve
33 Pent Rd
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Roughly 5 minutes away from our home, Devil's Den Preserve is a spectacular hiking and adventure location, for both friends and family alike. You can trek on more than 20 miles of trails, bringing you to waterfalls and high rocky ledges. If you love birdwatching, some 140 bird species have been recorded on this land, from pileated woodpeckers to ruffed grouses. If plants are more your thing, more than 500 kinds of trees and wildflowers grow here. My favorite part has always been the lake -- there's really nothing better than it in Fairfield County. Regardless, if the outdoors are what you're looking for, here's the place to be.

Food scene

The Whelk is a fantastic seafood restaurant (might be the best in the area) with sustainable local produce. I'd recommend the oysters & cocktails. You don't have to make a reservation, but I would recommend it. On a busy night, it can be very difficult to get a place because all the locals are here.
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The Whelk
575 Riverside Ave
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The Whelk is a fantastic seafood restaurant (might be the best in the area) with sustainable local produce. I'd recommend the oysters & cocktails. You don't have to make a reservation, but I would recommend it. On a busy night, it can be very difficult to get a place because all the locals are here.
Terrain has seasonally changing brunch, lunch, and dinner menus featuring hand-selected local produce, meats, and dairy alongside a thoughtfully curated beverage program from near and far. Served in a deliberately designed environment to blur the line between indoor and outdoor spaces, each cafe’s décor is unique, providing an inspiring dining experience every time. A bit pricy, but a great experience.
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Terrain Cafe
561 Post Rd E
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Terrain has seasonally changing brunch, lunch, and dinner menus featuring hand-selected local produce, meats, and dairy alongside a thoughtfully curated beverage program from near and far. Served in a deliberately designed environment to blur the line between indoor and outdoor spaces, each cafe’s décor is unique, providing an inspiring dining experience every time. A bit pricy, but a great experience.
Bar & Restaurant situated on the pedestrian only street in Westport CT. I've been here many times with my family and have nothing but great things to say about it. Our favorites have always been the Lobster Mac & Cheese and Scallops.
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Spotted Horse Tavern
26 Church Ln
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Bar & Restaurant situated on the pedestrian only street in Westport CT. I've been here many times with my family and have nothing but great things to say about it. Our favorites have always been the Lobster Mac & Cheese and Scallops.
A quaint, upscale restaurant & bar in Southport -- another wonderful idyllic quaint New England town close to Weston. This restaurant has a great vibe about it that I cannot really explain.
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Gray Goose
246 Old Post Rd
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A quaint, upscale restaurant & bar in Southport -- another wonderful idyllic quaint New England town close to Weston. This restaurant has a great vibe about it that I cannot really explain.

Entertainment

In the summer, the Levitt Pavilion hosts a wide range of artists, from Jazz to classical, all completely free to watch on a grass outdoor seating area. Make sure to bring some food and enjoy the show, as there's always one sure to be on.
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The Levitt Pavilion for the Performing Arts
40 Jesup Rd
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In the summer, the Levitt Pavilion hosts a wide range of artists, from Jazz to classical, all completely free to watch on a grass outdoor seating area. Make sure to bring some food and enjoy the show, as there's always one sure to be on.
Westport Country Playhouse is a not-for-profit local historical theater that has phenomenal performances all the time. The tickets are reasonably priced, making it worth a visit for an evening.
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Westport Country Playhouse
25 Powers Ct
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Westport Country Playhouse is a not-for-profit local historical theater that has phenomenal performances all the time. The tickets are reasonably priced, making it worth a visit for an evening.