Wilton

Day Trips

Make the most of your day with our curated plans, packed with Wilton's hidden gems and unique experiences!

day 1
Exploring Historic Center
morning
:

Start your day with a visit to the Wilton Historical Society, where you can immerse yourself in the rich local history through engaging exhibits. Afterward, take a leisurely stroll through the charming town center, admiring the beautiful colonial architecture and quaint shops. Don't forget to grab a coffee at a local café to fuel your exploration.

afternoon
:

In the afternoon, head to the Wilton Library for a unique blend of culture and education, featuring special exhibits and cozy reading nooks. Following your library visit, enjoy a picnic lunch at Merwin Meadows Park, surrounded by lush greenery and tranquil ponds. Take some time to walk the scenic trails, soaking in the peaceful atmosphere.

evening
:

As the sun sets, visit one of Wilton’s delightful restaurants for a farm-to-table dining experience, where you can savor locally sourced ingredients. After dinner, take a gentle walk around the historic district, enjoying the beautifully lit streets and the evening ambiance. End your night at a local coffee shop or ice cream parlor, indulging in a sweet treat while reflecting on your day.

day 2
Nature and Wildlife Exploration
morning
:

Begin your morning with a guided nature walk at the Wilton Nature Center, where you can observe local wildlife and learn about native plants. Bring your binoculars to spot birds and other creatures in their natural habitat while enjoying the serene surroundings. A light breakfast picnic by the pond will enhance your connection with nature.

afternoon
:

In the afternoon, venture to the nearby Merwin Meadows, where you can rent a kayak or canoe to explore the tranquil waters of the Saugatuck River. Enjoy the peaceful surroundings while paddling and keep an eye out for the diverse bird species that inhabit the area. Afterward, relax on the banks with a good book or simply take in the beauty of the landscape.

evening
:

As dusk approaches, return to town and enjoy a casual dinner at a family-friendly restaurant that offers outdoor seating. After your meal, attend a local event at the Wilton Library, such as a storytelling night or author reading, to engage with the community. Wind down your evening with a leisurely walk back to your accommodation, enjoying the stars that light up the clear sky.

day 3
Art and Culture Appreciation
morning
:

Start your day at the Wilton Arts Council, where you can participate in a morning art class or workshop led by local artists. Express your creativity while learning new techniques and connecting with fellow art enthusiasts. Afterward, visit the gallery to admire the works of local talents displayed throughout the space.

afternoon
:

For lunch, enjoy a meal at a nearby bistro that celebrates local flavors, then spend your afternoon exploring the various public art installations scattered around town. Take your time to photograph these unique pieces and appreciate the creativity that adorns the streets. If time permits, stop by a local craft shop to find a memento or two.

evening
:

In the evening, attend a live performance at the Wilton Playhouse, where you can enjoy a local theater production or musical show. The intimate setting makes for an engaging experience, allowing you to connect with the performers and their craft. After the show, gather with friends at a nearby bar or café to discuss your favorite moments of the evening.

day 4
Outdoor Adventure at Wilton Parks
morning
:

Kick off your day with a refreshing hike at the nearby Weir Farm National Historic Site, where you can explore beautiful trails that were once frequented by famous artists. The natural beauty and historical significance of the site make for an inspiring morning adventure. Pack a hearty breakfast to enjoy at one of the scenic viewpoints along the trail.

afternoon
:

After your hike, visit the Wilton Recreation Department to learn about various sports activities and facilities available. Engage in an afternoon of friendly competition with local residents, trying out sports like tennis or basketball. Take a break to enjoy lunch at a park picnic area, soaking in the sunshine and community vibes.

evening
:

As the day winds down, make your way to a local outdoor concert or movie night, where you can enjoy live music or a family-friendly film under the stars. Bring a blanket and some snacks for a cozy evening experience with fellow attendees. Conclude your day with a nightcap at a local bar, celebrating the camaraderie of your adventures.

day 5
Culinary Delights and Local Markets
morning
:

Begin your culinary exploration at the Wilton Farmers' Market, open on weekends, where you can sample fresh produce, artisanal foods, and handmade goods from local vendors. Engage with the farmers and learn about their sustainable practices while picking up some ingredients for a picnic later in the day. Enjoy a light breakfast from one of the food stalls for a taste of local flavors.

afternoon
:

After your market visit, participate in a cooking class at a local culinary school, where you can learn to prepare dishes using the fresh ingredients you purchased. This hands-on experience allows you to connect deeper with the food culture of Wilton. Enjoy the meal you’ve prepared together with your classmates, celebrating your newfound culinary skills.

evening
:

In the evening, dine at a renowned local restaurant known for its innovative cuisine that highlights seasonal ingredients. Savor a multi-course meal paired with select wines, immersing yourself in the local culinary scene. After dinner, consider joining a food tour that features local eateries and hidden gems, learning about the history and stories behind each stop.

day 6
Historical Sites and Scenic Drives
morning
:

Start your day with a visit to the Wilton Historical Society’s events, where you can participate in a guided tour of historical sites around the town. Learn about the rich heritage of Wilton and the stories of its founding families. Enjoy a light breakfast at a nearby café before heading out to the scenic drives.

afternoon
:

Take a picturesque drive through the Wilton countryside, stopping at historic landmarks and beautiful estates along the way. Explore the scenic routes that showcase the stunning New England landscape, complete with autumn foliage if you're visiting in the fall. Pack a lunch to enjoy at one of the many scenic overlooks that dot the area.

evening
:

As evening arrives, return to town for a historical reenactment or lecture at the local community center. Such events often feature local historians or actors bringing the past to life, making it a unique experience. Afterward, grab dinner at a restaurant that offers a history-themed menu, allowing you to enjoy a meal steeped in local culture.

day 7
Family Fun Day at Wilton Parks
morning
:

Kick off your family fun day at the Wilton Town Park, where the kids can enjoy the playground while you relax on the grass. Consider organizing a friendly game of soccer or frisbee to get everyone moving and involved. Bring along a breakfast picnic to keep everyone energized for the day's activities.

afternoon
:

In the afternoon, visit the nearby Wilton Recreation Center, where you can participate in family-friendly activities and sports together. Take advantage of the swimming pool or sign up for a family class that promotes teamwork and fun. After a busy afternoon, enjoy lunch at the center's café, where you can refuel before continuing your adventure.

evening
:

As the day comes to a close, enjoy a casual dinner at a family-oriented restaurant that offers a kid-friendly menu. Afterward, take a trip to the local bowling alley for some light-hearted competition that everyone can enjoy. Wrap up your day with ice cream from a local parlor, sharing laughs and highlights of your family fun day.

day 8
Wellness Retreat and Relaxation
morning
:

Start your day with a rejuvenating yoga session at one of Wilton's wellness studios, surrounded by nature and tranquility. Engage in meditation practices that help center your mind and prepare you for a day of relaxation. Enjoy a nutritious breakfast smoothie at a local café afterward, fueling your body for the day ahead.

afternoon
:

Spend your afternoon at a local spa, indulging in massages or wellness treatments that promote relaxation and rejuvenation. Take some time to unwind in a sauna or steam room, allowing your body to detox and recharge. A light lunch at the spa’s café will nourish you while you soak in the serene atmosphere.

evening
:

In the evening, attend a wellness workshop focused on mindfulness or nutrition, connecting with others who share similar interests. This interactive experience will provide you with practical tips to incorporate into your daily life for overall wellness. Conclude your day with a light dinner at a health-conscious restaurant, enjoying dishes crafted from fresh, local ingredients.

Discover Wilton

Read more in our Wilton 2025 Travel Guide.

Wilton Travel Guide