Windham County, Vermont Travel Guide

Discover Windham County, Vermont: A perfect blend of outdoor adventure, charming small towns, and rich cultural heritage in New England's picturesque landscape.

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Windham County

Nestled in the southeastern corner of Vermont, Windham County is a picturesque destination that embodies the quintessential New England experience. With its rolling hills, charming small towns, and vibrant cultural scene, it offers a perfect blend of natural beauty and rich history. Visitors can explore the historic downtowns of Brattleboro and Bellows Falls, where they will find an array of unique shops, art galleries, and farm-to-table restaurants. The county is also home to many festivals and events, celebrating everything from music and art to local agriculture and seasonal traditions. Outdoor enthusiasts will find plenty to do in Windham County, which boasts some of the best hiking, biking, and skiing opportunities in the region. The Green Mountain National Forest provides a stunning backdrop for a variety of activities, with trails that cater to all skill levels. In the winter, the area transforms into a snowy paradise, attracting skiers and snowboarders to popular resorts like Mount Snow and Stratton Mountain. For a more leisurely experience, visitors can take a scenic drive along the Connecticut River or enjoy a peaceful afternoon at one of the many local parks and nature reserves. Windham County's rich cultural heritage is reflected in its numerous historic sites and museums. The Estey Organ Museum in Brattleboro showcases the town's storied manufacturing past, while the Rockingham Meeting House offers a glimpse into 18th-century colonial life. Throughout the county, visitors will find beautifully preserved covered bridges, quaint churches, and historic inns, providing a sense of stepping back in time. Whether you're seeking adventure, relaxation, or a taste of New England history, Windham County promises an unforgettable experience.

From Eve

Know before you go

Hi, I'm Eve. Here are a few practical things to know before exploring Windham County.

Visit during fall for stunning foliage; the colors are breathtaking.
Try local cheeses and maple syrup at farmers' markets for an authentic taste of Vermont.
Book accommodations early during ski season; resorts fill up fast.
Explore local art galleries in Brattleboro for unique souvenirs.
Check the local event calendar for festivals and fairs during your stay.

Top City Travel Guides in Windham County

The cities of Windham County, and the easiest places to base yourself.

Brattleboro

Bennington

Destinations in Windham County

Resorts, valleys and scenic spots worth a trip of their own.

Okemo Mountain Resort

Bennington Battle Monument

Emerald Lake State Park

Molly Stark State Park

Mount Equinox

Explore Windham County: Things to Do, Places to Eat, Hotels & More

Handpicked recommendations for top attractions, local dining, accommodations, and more

Top Attractions & Sightseeing in Windham County

Top-rated picks

Best Attractions

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All Attractions

Stratton Mountain Resort

Discover the all-season allure of Stratton Mountain Resort, where skiing, hiking, and golfing meet stunning landscapes in Vermont's picturesque Green Mountains.

4.5

Magic Mountain Ski Area

Experience thrilling skiing, live music, and beautiful views at Magic Mountain Ski Area, Vermont's top destination for winter fun and adventure.

4.7

Creamery Covered Bridge

Experience the historical beauty of Creamery Covered Bridge in Brattleboro, Vermont, a picturesque landmark surrounded by nature's charm.

4.6

Living Memorial Park

Experience the natural beauty and recreational charm of Living Memorial Park in Brattleboro, Vermont, a perfect escape for tourists and nature lovers.

4.6

Best landmarks in Windham County

Top-rated picks

Best Landmarks

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All Landmarks

Bennington Battle Monument

Discover the Bennington Battle Monument, a historic tribute to the American Revolution with stunning views and rich history in Vermont.

4.6

Hildene, The Lincoln Family Home- Welcome Center

Explore Hildene, The Lincoln Family Home, a historical treasure in Vermont blending heritage, stunning gardens, and captivating architecture.

4.7

Magic Mountain Ski Area

Experience thrilling skiing, vibrant nightlife, and breathtaking views at Magic Mountain Ski Area in Londonderry, Vermont, the ultimate winter getaway.

4.7

Marsh-Billings-Rockefeller National Historical Park

Experience the beauty and history of Marsh-Billings-Rockefeller National Historical Park, a remarkable blend of nature, conservation, and cultural heritage in Vermont.

4.7

Best restaurants in Windham County

Top-rated picks

Best Restaurants

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The Marina

Experience fresh seafood with stunning waterfront views at The Marina in Brattleboro, Vermont - your go-to destination for American cuisine.

4.2

Ye Olde Tavern

Discover Ye Olde Tavern: A quintessential American dining experience blending rustic charm with gourmet flavors in Manchester Center.

4.6

1846 Inn & Tavern

Experience rustic charm and culinary delights at 1846 Inn & Tavern in West Dover, Vermont – your gateway to adventure and relaxation.

4.4

Yalla Vermont

Experience authentic Mediterranean flavors at Yalla Vermont in Brattleboro - where every dish tells a story.

4.8

Best bars in Windham County

Top-rated picks

Best Bars

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All Bars

Rail and River Tavern

Experience Vermont's culinary charm at Rail and River Tavern, where hearty meals and local brews create the perfect dining escape.

4.0

Ye Olde Tavern

Experience the flavor of Vermont at Ye Olde Tavern, a fine dining American restaurant offering locally-sourced dishes in a cozy setting.

4.6

MacLaomainn's Scottish Pub

Discover the charm of Scotland at MacLaomainn's Scottish Pub in Chester, Vermont, where delicious food and craft beers await.

4.5

Anchor Seafood Restaurant

Experience the best in seafood dining at Anchor Seafood Restaurant in Wilmington, Vermont, where fresh flavors and friendly service await.

4.4

Best shops in Windham County

Top-rated picks

Best Shops

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The Vermont Country Store Rockingham

Experience the heart of Vermont at The Vermont Country Store, a general store offering local crafts, delicious treats, and a nostalgic shopping experience.

4.6

The Vermont Country Store Weston

Experience the charm and nostalgia of The Vermont Country Store, a must-visit destination for unique crafts and local delicacies in Weston.

4.6

Hogback Mountain Country Store

Explore Hogback Mountain Country Store for unique Vermont gifts, local snacks, and stunning mountain views in a charming gift shop.

4.7

The Newfane Store

Experience the charm of Vermont at The Newfane Store, where unique gifts and delicious deli delights await every visitor.

4.7

Explore Windham County on the Map

A handpicked selection of must-see spots in Windham County, mapped for you.

Windham County Essentials

Windham County is located in the southeastern part of Vermont. The nearest major airports are Bradley International Airport in Hartford, Connecticut, and Manchester-Boston Regional Airport in New Hampshire, both approximately 2 hours away by car. From these airports, you can rent a car or take a shuttle service to reach Windham County. Alternatively, Amtrak offers train services to Brattleboro, one of the major towns in Windham County, from various locations including New York City and Washington D.C.
Within Windham County, the best way to get around is by car. Renting a car is highly recommended for flexibility and ease of travel. Public transportation is limited, but the MOOver bus service offers routes connecting Brattleboro, Wilmington, and other towns in the area. Biking is also a popular option, especially during the warmer months. Taxis and rideshare services like Uber and Lyft are available but may have limited availability in more rural areas.
The official currency in Windham County is the US Dollar (USD). Credit and debit cards are widely accepted in most establishments, including hotels, restaurants, and shops. However, it is advisable to carry some cash, especially when visiting smaller towns and rural areas where card payment options may be limited. ATMs are available in larger towns like Brattleboro and Bellows Falls.
Windham County is generally a safe destination for tourists. However, it is always wise to take common-sense precautions. Avoid leaving valuables in your car and be cautious when walking alone at night in unfamiliar areas. Brattleboro, the largest town in the county, has a low crime rate, but like any place, it is advisable to stay aware of your surroundings.
In case of an emergency, dial 911 for immediate assistance. Windham County has several medical facilities, including Brattleboro Memorial Hospital and Grace Cottage Family Health & Hospital in Townshend. It is recommended to have travel insurance that covers medical emergencies. Pharmacies are available in larger towns for minor health issues and over-the-counter medications.
Fashion: Do dress in layers, as the weather can be unpredictable. Comfortable walking shoes are a must. Avoid overly formal attire unless attending a special event. Religion: Do respect local customs and traditions, especially when visiting places of worship. Public Transport: Do be respectful to drivers and fellow passengers. Don’t eat or drink on public transport. Greetings: Do greet people with a friendly 'hello' or 'hi'. Vermonters are generally friendly and open. Eating & Drinking: Do try local foods and beverages, such as Vermont cheddar cheese and maple syrup. Don’t leave without tipping your server; 15-20% is customary in restaurants.
To experience Windham County like a local, visit the Brattleboro Farmers' Market, where you can buy fresh produce and local crafts. Engage with locals at community events like the Strolling of the Heifers parade. For outdoor enthusiasts, hiking in the Green Mountain National Forest or skiing at Mount Snow offers a true taste of Vermont’s natural beauty. Don't miss the chance to visit local breweries and distilleries to sample craft beers and spirits made in the region.

When is the best time to visit Windham County?

With Eve

Useful Local Phrases for Windham County

You don't need to speak the language perfectly. Even learning a few simple words can make conversations warmer—and locals usually appreciate the effort.

— Eve

6 phrase groups English + pronunciation

Here are the phrases I use most often in Windham County. Try a few—you'll be surprised how far they go! 😊
❤️

- HelloHowdy
  [How-dee]
- GoodbyeSee ya later
  [See ya lay-tur]
- YesYup
  [Yup]
- NoNope
  [Nope]
- Please/You’re welcomeSure thing
  [Shur thing]
- Thank youThanks a lot
  [Thangs a lot]
- Excuse me/SorryPardon me
  [Pardon me]
- How are you?How’s it going?
  [How’s it goin'?]
- Fine. And you?Good. And you?
  [Good. And you?]
- Do you speak English?Do ya speak English?
  [Doo ya speak English?]
- I don’t understandI’m not following
  [I’m not followin']
- I’d like to see the menu, pleaseCould I see the menu, please?
  [Could I see the men-yoo, please?]
- I don’t eat meatI’m a vegetarian
  [I’m a vege-tair-ee-an]
- Cheers!Cheers!
  [Cheers!]
- I would like to pay, pleaseCan I get the check, please?
  [Can I get the check, please?]
- Help!Help!
  [Help!]
- Go away!Leave me alone!
  [Leave me alone!]
- Call the Police!Call the cops!
  [Call the cops!]
- Call a doctor!Get a doctor!
  [Get a doctor!]
- I’m lostI can’t find my way
  [I can’t find my way]
- I’m illI’m not feeling well
  [I’m not feelin' well]
- I’d like to buy...I’d like to grab...
  [I’d like to grab...]
- I’m just lookingJust browsing, thanks
  [Just browsin', thanks]
- How much is it?What’s the price?
  [What’s the price?]
- That’s too expensiveThat’s a bit pricey
  [That’s a bit pricy]
- Can you lower the price?Can ya do any better on the price?
  [Can ya do any better on the price?]
- What time is it?What’s the time?
  [What’s the time?]
- It’s one o’clockIt’s one o'clock
  [It’s one o'clock]
- Half past (10)Half past ten
  [Half past ten]
- MorningMorning
  [Morning]
- AfternoonAfternoon
  [Afternoon]
- EveningEvening
  [Evening]
- YesterdayYesterday
  [Yesterday]
- TodayToday
  [Today]
- TomorrowTomorrow
  [Tomorrow]
- 1One
  [One]
- 2Two
  [Two]
- 3Three
  [Three]
- 4Four
  [Four]
- 5Five
  [Five]
- 6Six
  [Six]
- 7Seven
  [Seven]
- 8Eight
  [Eight]
- 9Nine
  [Nine]
- 10Ten
  [Ten]
- Where's a/the...?Where’s the nearest...?
  [Where’s the nearest...?]
- What’s the address?What’s the address?
  [What’s the address?]
- Can you show me (on the map)?Can ya point it out on the map?
  [Can ya point it out on the map?]
- When's the next (bus)?When’s the next bus?
  [When’s the next bus?]
- A ticket (to ....)A ticket to...
  [A ticket to...]

History of Windham County

Windham County was founded in 1781, making it one of the earliest established counties in Vermont. The county was named after Windham, Connecticut, reflecting the origins of many of its early settlers. The early economy was primarily based on agriculture, with settlers taking advantage of the fertile soil and ample water supply.
Although the Battle of Bennington took place in nearby Bennington County, its effects were felt throughout Windham County. This pivotal Revolutionary War battle in 1777 was a significant victory for the American forces and boosted the morale of the settlers in Windham County. Many local men participated in the battle, and their contributions were celebrated for years to come.
Windham County experienced significant growth during the Industrial Revolution. The presence of rivers and streams made it an ideal location for mills and factories. Towns like Brattleboro became industrial hubs, producing goods ranging from textiles to paper. The arrival of the railroad in the mid-19th century further facilitated commerce and population growth.
The Estey Organ Company, founded in Brattleboro in 1846, became one of the largest and most influential organ manufacturers in the United States. The company produced reed organs and later, pipe organs, which were shipped worldwide. The Estey Organ Company was a major employer in Windham County and played a significant role in the cultural and economic development of the region.
Founded in 1834, the Vermont Asylum for the Insane, now known as the Brattleboro Retreat, was one of the first mental health facilities in the United States. It was established by Anna Marsh, a local philanthropist, and provided progressive and humane treatment for its patients. The institution remains a significant part of Windham County's history and continues to operate today.
Windham County, like much of Vermont, was devastated by the Great Flood of 1927. Torrential rains caused rivers to overflow, resulting in widespread destruction of homes, bridges, and roads. The flood had a lasting impact on the county's infrastructure and led to significant changes in flood control and land management practices.
In the 20th century, Windham County began to attract tourists seeking natural beauty and outdoor recreation. The Green Mountains and the Connecticut River offered opportunities for hiking, skiing, and boating. Towns like Wilmington and Dover became popular destinations for winter sports enthusiasts, contributing to the county's economy and cultural landscape.
Windham County hosts a variety of cultural festivals and events that celebrate its rich heritage. The Marlboro Music Festival, established in 1951, is one of the most prestigious classical music festivals in the country. The Strolling of the Heifers, an annual parade in Brattleboro, highlights the importance of agriculture and local food. These events draw visitors from far and wide, showcasing the county's vibrant community spirit.
Efforts to preserve Windham County's historical sites have been ongoing for decades. The Rockingham Meeting House, built in 1787, is one of the oldest and best-preserved public buildings in Vermont. The Windham County Historical Society, along with other local organizations, works tirelessly to maintain and promote the county's historical landmarks, ensuring that its rich history remains accessible to future generations.