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The skyline of Montpelier in Vermont.

9 Most Comfortable Towns in Vermont for Seniors

Welcome to the land of maple syrup, artisan cheese, craft beer, and the birthplace of Ben & Jerry's. The vibe that Vermont has to offer is unmatched. Give your tastebuds and tummy the treatment they deserve. If you stick around until autumn, you will also witness the most breathtaking and magazine-worthy fall foliage. Hidden behind the views and activities are many comfortable communities offering great healthcare, affordable living, and a sense of camaraderie, perfect for retirement. From Woodstock's striking atmosphere to Stowe's adventurous mountains, Vermont has the perfect, comfortable town to begin your next chapter.

Burlington

Church Street in downtown Burlington, Vermont.
View of Church Street in downtown Burlington, Vermont. Editorial credit: julie deshaies / Shutterstock.com

Situated by Lake Champlain, Burlington is a visual and soothing masterpiece. Despite being the largest city in the state, Burlington still offers that charming small-town feel. Rest assured, you are in good hands here. The area is home to The University of Vermont Medical Center, a high-quality, award-winning, and top-rated facility. Cardiology, cancer care, and orthopedics are just some of the many specialty areas of the healthcare giant.

Burlington welcomes seniors to ditch their cars as the town boasts an incredible public transportation system. Green Mountain Transit has your back wherever you need to go, offering accessible service to everyone. A reduced fare is granted to seniors and passengers with disabilities. Experience the pinnacle of luxury and VIP treatment with the on-demand service from MyRide by GMT.

Burlington's alluring downtown area is very walkable, another phenomenal option for those without a vehicle. Shop and dine to your heart's content and check out local events and markets, all within walking distance. The Crow Bookshop is a must, where you can have the coziest read in the most magical interior. Live your best life with waterfront dining at The Skinny Pancake, where the crepes are a local favorite. Retirees can also relive their youthful days at the Burlington Discover Jazz Festival, an event full of dance and music.

Woodstock

Fall foliage in Woodstock, Vermont.
A rustic barn and church during autumn in the town of Woodstock, Vermont. Editorial credit: MindStorm / Shutterstock.com

If you are looking to live somewhere with magazine-worthy scenery, look no further than Woodstock. Every single area in this stunning town is a captivating escape, and pictures do not do it justice. From the end of September through October, the area is bursting with autumnal colors of reds, oranges, and gold. Being a hotspot for natural beauty, ample opportunities exist to keep seniors fit while taking in one’s surroundings. Hikers can conquer 20 miles of trails at Marsh-Billings-Rockefeller National Historical Park. After an excursion, one can ease their legs off in the bountiful gardens at Marsh-Billings-Rockefeller.

Woodstock is enchanting to explore on wheels. Rent an e-bike through Woodstock Wheels and use the pre-mapped routes available on your phone. The self-guided tour lets you enjoy Woodstock's atmosphere at your own pace. While housing prices are higher, retirees can settle down on a budget at the Woodstock Terrace. This assisted living facility offers memory care, private accommodations, and a dedicated team of care professionals.

Middlebury

View of Middlebury Falls in the town of Middlebury, Vermont.
View of Middlebury Falls in the town of Middlebury, Vermont.

On the outskirts of Vermont's famous Green Mountains, you will find the welcoming town of Middlebury. Those looking to buy a house can consider many options thanks to the median housing value of $435,000, which is just $50,000 more than the state average. That said, if the price seems steep, plenty of senior living areas, such as EastView at Middlebury, offer independent living and assisted living with amenities like regular meals, healthcare, and social programs.

When it comes to a lively arts and culture scene, Middlebury is top-notch. Enjoy live theatre, music performances, and seasonal events at the Town Hall Theatre. The establishment has a solid five stars on TripAdvisor and is loved by locals and visitors. One can also support aspiring local talent by checking out The Edgewater Gallery. Do not forget to check out the gallery's engaging events, such as the Winter Weekend of Art, Music, and Cheer. For a fresh new take on the art Â鶹AV, see the ever-changing exhibits at the Middlebury College Museum of Art. The college features six to eight temporary exhibitions each year alongside a permanent collection. Moreover, the campus at Middlebury College is an art exhibit in itself, with its exquisite architecture and manicured grounds.

Waterbury

Aerial view of Waterbury in Vermont during autumn.
Aerial view of Waterbury in Vermont during autumn.

For retirees seeking a lively community with a love for food and culture, Waterbury offers an ideal blend of charm and activity. The town hosts a variety of events, from Polish Potato Pierogi Workshops and wine tastings to Bluegrass Night at Pro Pig. Foodies will find plenty to enjoy, including the Cold Hollow Cider Mill, where one can savor homemade apple cider, legendary cider donuts, and local maple syrup. Feeling indulgent? Try all three! Craft beer enthusiasts can head to Reservoir, a local favorite featuring 35 craft beers to sample. The Ben & Jerry's ice cream factory on Route 100 is another must-visit, offering a glimpse into the birthplace of their famous flavors.

Waterbury is home to a thriving senior population, with nearly 20% of its residents aged 65 and older. The Waterbury Area Senior Center serves as a hub for social and recreational activities. Seniors can participate in exercise classes, enjoy coffee mornings, or join in games like bingo and dominoes. The center also provides nutritious meals through its monthly menu and Meals on Wheels program, ensuring dining is both convenient and satisfying. Public transportation, including Green Mountain Transit, makes it easy for residents to navigate the area, whether for errands or appointments. Healthcare is also readily accessible, with clinics such as the Central Vermont Medical Center providing essential medical support.

Fair Haven

Main Street in Fair Haven, Vermont.
Rustic brick buildings along Main Street in Fair Haven, Vermont. By Jared and Corin - Fair Haven, Vermont main street, CC BY-SA 2.0, .

Fair Haven makes an incredible retirement destination if affordability is a top priority. The town boasts a median housing value of $230,000, which is $150,000 less than the state average. To this end, retirees can purchase their dream home without breaking the bank. While you might want to spend all your time at home, the nearby Castleton Amtrak Station offers intercity transport for any out-of-station requirements.

Regarding local activities, Fair Haven is a haven of the outdoors. Retirees will love basking in nature and taking it easy at Half Moon Pond State Park. Lose yourself in the lush forest and hike along the many trails for all skill levels. One can also rent a cabin or cottage, pitch a tent, or park your RV for a secluded home away from home. Fair Haven is also an immaculate fishing hotspot. Coast through the open waters with a tranquil fishing session through Cedar Mountain Fishing Guide. Glide through Lake Bomoseen or Lake Champlain with these incredible guided tours. If you would rather skip the fishing, seniors will be happy to know that Cedar Mountain Fishing offers lake tours.

Stowe

Aerial view of Stowe in Vermont.
Aerial view of Stowe in Vermont.

Grab your winter gear and head to Stowe, Vermont, a legendary ski town that transforms into a winter wonderland yearly. Nestled in the Green Mountains, Stowe offers endless opportunities for skiing and snowboarding, as well as relaxing frosty adventures. Outdoor enthusiasts will find year-round activities to enjoy, making it an excellent spot for retirees who love nature. Take in the panoramic views from Vermont's highest peak, Mount Mansfield, at the Stowe Mountain Resort, where you can enjoy a relaxing cross-country ski or indulge in a slopeside spa experience. The gondola and ski lifts make it easy to get to the top with minimal effort. For those who prefer to hike, scenic trails like Moss Glen Falls, Stowe Pinnacle Trail, and Bingham Falls Trail provide a perfect way to bask in nature. Alternatively, you can pedal through Stowe’s picturesque surroundings with a unique bike tour from 4 Points VT, a highly-rated experience you won’t forget.

While housing in Stowe is on the pricier side, retirees can find comfort and community at The Woodlands at Stowe, an assisted living center. Residents enjoy chef-prepared meals, including delights like Chicken Cordon Bleu, Beef Barley Soup, and Carrot Cake, with a menu that constantly changes to keep things fresh. The town itself is highly accessible, with most businesses—such as Bear Pond Books, Black Cap Coffee & Bakery, and Union Bank—within walking distance. For added convenience, Stowe is bike-friendly and offers a free shuttle service via Green Mountain Transit, making exploring this charming mountain town easy.

Bennington

Vermont's first Protestant Church in Bennington, Vermont.
The "Old First" Congregational Church in Bennington, Vermont. Editorial credit: Brian Logan Photography / Shutterstock.com

Bennington offers the perfect blend of rich history and upscale living, making it an ideal place for seniors to settle down. As Vermont's oldest town, founded in the 18th century, it boasts a timeless charm. Capture memorable photos at iconic covered bridges like Silk Road and Paper Mill, which provide enchanting backdrops and are marvels of craftsmanship. For history enthusiasts, visiting the Park-McCullough Historic Governor’s Mansion is a must. This 1864 Victorian-style masterpiece is as stunning inside as it is outside. And that’s just the beginning—Bennington is brimming with historical sites waiting to be explored.

For a comfortable and fulfilling retirement, consider Brookdale Fillmore Pond, voted Best Assisted Living by U.S. News. Whether you prefer independent living or need assistance, Brookdale offers exceptional accommodations and amenities. Everything you need is close, including a general store, hairdresser, and clinic. The vibrant activity calendar ensures there’s never a dull moment. Try yoga or Tai Chi to enhance your well-being, or tap into your creative side with cooking or painting classes. Socialize with new friends at the onsite sports bar, fireside living room, or sunroom. If you ever need specialized medical care, the nearby Southwestern Vermont Medical Center has an emergency room, nursing home, and state-of-the-art machinery to keep you healthy.

Montpelier

View of fall foliage and buildings in downtown Montpelier, Vermont.
View of fall foliage and buildings in downtown Montpelier, Vermont.

Regardless of where you go in Vermont, you will experience the beauty of seasonal changes. Winter in Vermont is inevitable; however, Montpelier, the state capital, has a milder climate than other areas. Summer here sees an average daily high temperature above 78°F, while winter sees an average daily high temperature around 27°F. The median home value is $396,000, which is a steal for the incredible mountain scenery and bustling neighborhoods.

Despite being the state capital, Montpelier only has a population of around 8,000, according to U.S. Census data. This makes it a comfortable town for those who want to avoid large crowds. Ditch the car because downtown Montpelier is very walkable. Stroll to anything from restaurants, galleries, shops, and historical landmarks. Support local by checking out handmade crafts at Artisans Hand Craft Gallery, an award-winning Vermont treasure. Seniors will love filling their fridge and pantry with fresh produce from the Farmer's Market. If you’re feeling lazy, try fresh and seasonal specialties at the North Branch Cafe. After a hearty meal, plenty of local landmarks such as the Vermont Historical Society Museum and Vermont State House keep days entertaining in town.

Newport

View of Newport along the coast of Lake Memphremagog in Vermont.
View of Newport along the coast of Lake Memphremagog in Vermont.

Newport is a picturesque lakeside gem that embodies the cozy charm of New England living. Rooted in a strong farming heritage, this welcoming town is a fantastic choice for seniors seeking a well-rounded lifestyle. Its proximity to the Canadian border—less than a 30-minute drive—adds an international flair, making it easy to visit friends up north. Adventure awaits in Newport with a wealth of outdoor activities, from skiing and golfing to fishing, biking, and kayaking. Lake Memphremagog is perfect for serene fishing trips, or you can rent a kayak at Prouty Beach to explore its tranquil waters. For land-based activities, Bluffside Farm offers scenic trails for walking or cross-country skiing in the winter, letting you enjoy Vermont's natural beauty year-round.

After all that activity, keeping your health in check is a breeze. Conveniently located in town, North Country Hospital provides a wide range of services, including radiology, dialysis, cardiology, and sleep disorder treatments. With excellent healthcare at your fingertips, you can stay in top shape and fully embrace the joys of retirement in Newport. It is also one of the most affordable towns on this list, with an average home value of less than $250,000.

Consider the Cozy Comfort of Vermont for Retirement

Retirement should be a comfortable journey, and there are many towns in Vermont to make that happen. Experience top-tier healthcare and savor chauffeur service with Burlington's incredible public transportation system. Step into a magazine-worthy retirement in Woodstock or enjoy affordable living in Fair Haven. Montpelier welcomes you with a comfortable climate and walkable downtown. You may decide to fuel your active lifestyle in Stowe or eat your heart out with the strong senior community in Waterbury. Bennington is a seamless blend of history and luxury, while Middlebury has a lively arts culture. If you are stuck, Newport is a well-rounded town paired with everything you need. Regardless of your choice, plenty of comfortable Vermont towns are ready for your new home.

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