Inn on Putney Road Bed and Breakfast – Brattleboro, Vermont
Best Mountain Biking Trails in Vermont
Best Mount Snow Bike Park Guide for Summer Riders
If you’re dreaming of an unforgettable Vermont summer adventure, Mount Snow Bike Park should be at the top of your list. Nestled in the heart of Mount Snow Vermont, this lift-served destination transforms the mountain into a playground for riders of every level. First-timers will love the wide, welcoming green trails, while seasoned riders can push their limits on advanced routes packed with berms, flowing rock sections, and expertly crafted jumps. It’s no surprise this park is consistently celebrated as one of the best mountain biking destinations in Vermont.
The experience goes well beyond the trails. Spend a full day lapping runs with lift access, rent gear on-site, grab a bite between rides, or simply soak in the stunning chairlift views. There’s also hiking nearby for anyone who wants to mix up their day, making it a perfect outing for groups with different interests.
When you’re ready to explore off the mountain, Brattleboro is waiting to welcome you. There are so many things to do in Brattleboro: stroll through a thriving arts scene, browse one-of-a-kind local shops, savor meals at beloved independent restaurants, or take a peaceful walk along the Connecticut River. The town has an energy that’s creative, laid-back, and deeply welcoming, making it an ideal complement to a day on the mountain. It’s also a fantastic gateway to even more Vermont bike trails if you want to extend your riding adventure.
From the thrilling descents of Mount Snow Bike Park to Brattleboro’s charming streets and everything in between, this is a summer getaway that genuinely has it all. Come see why southern Vermont keeps drawing riders and explorers back, season after season.
Brattleboro Vermont Hotels Near Mount Snow Bike Park
After an exhilarating day, you deserve a place to truly unwind. Inn on Putney Road offers a beautifully refined stay that goes hand in hand with the surrounding landscape. What makes this a stand out among Brattleboro Vermont Hotels for active travelers is direct access to the Retreat Trails network, meaning you can keep exploring Vermont mountain biking and scenic walking paths right from the property. Wake up each morning to a delicious gourmet breakfast before heading out to ride, discover, or simply relax.
Best Things to Do in New England for a Winter Getaway
The Best Things to Do in New England this Winter
Winter reveals a quieter, more rewarding side of travel, and the best things to do in New England during the colder months go far beyond skiing alone. Snowy villages, cultural attractions, and outdoor experiences create the perfect backdrop for winter weekend getaways in Vermont. From scenic back roads to lively small towns, this season invites travelers to slow down and explore.
Southern Vermont is an excellent place to experience Northeast winter vacations, especially around Brattleboro. Located near the borders of New Hampshire and Massachusetts, this town offers easy access to outdoor recreation while maintaining a strong sense of local character. Days here can be filled with exploration, followed by evenings spent dining, listening to live music, or relaxing indoors.
One of the best places to visit in New England during winter is Mount Snow, just a short drive from Brattleboro. Skiing and snowboarding attract visitors from across the region, but non-skiers will also enjoy tubing, snowshoeing, and scenic gondola rides. Back in town, downtown Brattleboro provides a more relaxed pace with bookstores, galleries, and locally owned shops.
Outdoor enthusiasts will appreciate the Retreat Trails, a wooded network just minutes from downtown, ideal for snowshoeing or cross-country skiing. For a unique local tradition, the Harris Hill Ski Jump hosts one of the longest-running ski jumping events in the country, drawing spectators each winter. Nearby villages like Chester add even more charm, offering historic architecture and inviting lunch spots within easy driving distance.
A Cozy Place to Stay in Brattleboro, VT
Choosing the right lodging makes winter travel more enjoyable, especially for couples and adults seeking comfort and convenience. Boutique hotels in Brattleboro, VT, place guests close to the best things to do in New England while offering a more personal experience. The Inn on Putney Road offers welcoming guest rooms, a satisfying breakfast each morning, and a location that lets visitors spend the crisp winter days outside and warm, cozy evenings by the fire.
Whether you are planning a short winter escape or a more extended seasonal stay, Brattleboro offers a thoughtful mix of adventure, culture, and relaxation. Winter is an ideal time to discover the best things to do in New England and create a getaway worth repeating.
Exploring the Unique Castle Ruins near Brattleboro
Visit the Castle Ruins in Madame Sherri Forest
Exploring the castle ruins in Madame Sherri Forest is one of the most unique things to do in Vermont, offering a blend of history, architecture, and scenic hiking just outside Brattleboro. Located in nearby West Chesterfield, New Hampshire, this destination draws visitors with its unusual setting and the remains of a once-grand summer home hidden within the forest.
The trail to Madame Sherri’s Castle follows the Ann Stokes Loop, a manageable two-mile route that winds through a dense hemlock forest before revealing the site’s most recognizable feature, a sweeping stone staircase that rises unexpectedly into the trees. As you continue through the grounds, the remaining stonework, including columns, archways, and a large fireplace, provides a clear sense of the home’s original scale and design. These castle ruins stand as one of the most memorable landmarks in southern New England.
Madame Sherri’s house was commissioned by Antoinette Bramare, a French-born costume designer who built a name for herself in New York’s theater scene. In the late 1920s, she transformed this quiet landscape into a gathering place known for elaborate parties and distinctive architecture that blended European influences. After financial challenges forced her to leave, the property was abandoned and later destroyed by fire in 1962. Today, the preserved ruins and surrounding forest offer both historical context and a distinctive outdoor experience.
Beyond the castle ruins, the surrounding area adds depth to any visit. Extending your hike leads to Indian Pond and open ledges with expansive views, while nearby Brattleboro offers galleries, restaurants, and local markets. This combination makes it easy to pair outdoor exploration with cultural experiences, creating a well-rounded itinerary on a romantic getaway to Vermont!
Brattleboro, Vermont Boutique Hotels
After a day spent exploring Madame Sherri Forest, returning to one of the boutique hotels in Brattleboro, Vermont, provides a comfortable and thoughtfully designed retreat. The Inn on Putney Road offers a refined setting with carefully appointed guest rooms, inviting common spaces, and well-maintained gardens, creating a welcoming atmosphere.
Guests can begin their mornings with a gourmet breakfast and spend quiet time outdoors before heading out to explore more of the region. Its location within walking distance of downtown Brattleboro allows easy access to shops, dining, and the local arts scene, while still providing a peaceful place to unwind. Plan your visit to these castle ruins and reserve your stay to experience one of the most distinctive and engaging destinations in Vermont.
Hikes Near Brattleboro Vermont
Best Pisgah State Park Trails and Scenic Summer Hikes
Pisgah State Park is one of the most rewarding outdoor destinations in New England, especially for travelers planning a summer adventure near Brattleboro, Vermont. Located just across the state line in southwestern New Hampshire, this expansive 13,300-acre preserve is the largest in the New Hampshire state parks system and offers nearly 62 miles of multi-use trails through dense forest, wetlands, ponds, and highland ridges. For visitors searching for hikes near Brattleboro VT, this park provides exceptional trail variety without the crowds often found at more heavily visited parks.
The park’s six trailheads create easy access to routes for nearly every skill level. The Pisgah Mountain Loop remains one of the most popular options, offering an 8.5-mile route with scenic woodland terrain and rewarding ridge views. Travelers looking for a shorter outing often choose the Kilburn Pond and John Summers Trail, an approachable hike that winds through shaded forest before arriving at a peaceful swimming area during the warmer months.
Experienced hikers can challenge themselves on the Old Chesterfield, Chestnut Hill, Dogwood Swamp, and Southwoods Trail system, a longer route with notable elevation gain and quieter stretches of backcountry terrain. Summer mornings are particularly beautiful here, with soft light filtering through the forest canopy and noticeably quieter trails on weekdays.
Visitors exploring Pisgah State Park trails and the surrounding Southern Vermont region will find no shortage of outdoor activities nearby. Mount Wantastiquet, Mount Monadnock, Molly Stark State Park, and Chesterfield Gorge Natural Area all make excellent additions to a multi-day itinerary focused on hiking and scenic drives.
Unique Places to Stay in Vermont Near Pisgah State Park
For travelers searching for unique places to stay in Vermont after a full day outdoors, the Inn on Putney Road offers a refined and comfortable retreat just minutes from downtown Brattleboro. This historic 1931 French Baronial manor features six thoughtfully designed guest rooms, gourmet breakfasts prepared fresh each morning, and direct access to more than 17 miles of maintained hiking trails adjacent to the property. Its location makes it easy to experience the best things to do near Brattleboro VT while returning each evening to a quiet and welcoming setting.
Whether you are planning a weekend hiking escape or a longer summer adventure through New Hampshire state parks and Southern Vermont, Pisgah State Park is well worth adding to your itinerary.
Leaf Peeping in Southern Vermont
Best Fall Foliage Adventures in New England
As summer gives way to crisp autumn days, Brattleboro becomes one of the best places to experience fall foliage in New England. Located in southern Vermont, this welcoming town offers colorful mountain views, scenic backroads, and inviting small-town charm, making it an ideal destination for a couples getaway. Whether you prefer hiking to panoramic overlooks or enjoying a leisurely drive through the countryside, there are countless things to do in Brattleboro.
One of the most common questions travelers ask is, when is peak fall foliage in Vermont? While weather conditions influence the timing each year, the general pattern remains consistent. Color begins appearing in northern Vermont and at higher elevations during mid to late September before gradually moving south. In Brattleboro and the surrounding region, peak fall foliage typically arrives during the second half of October, giving visitors a longer opportunity to enjoy vibrant landscapes throughout the season.
Outdoor enthusiasts will find no shortage of places to admire the changing leaves. Popular destinations include the Retreat Trails, Fort Dummer State Park, Wantastiquet Mountain, Hogback Mountain Conservation Area, Putney Mountain, and the Ledges Overlook Trail. Each offers a unique perspective of the rolling hills covered in brilliant shades of red, orange, and gold.
Drivers can also experience spectacular scenery along the Molly Stark Scenic Byway, the Connecticut River National Byway, Scenic Route 100, the Shires of Vermont Byway, and the drive between Brattleboro and Mount Snow. Covered bridges, working farms, and classic New England villages make every mile memorable during fall.
Stay at a Charming Brattleboro Bed and Breakfast
The Inn on Putney Road provides an exceptional home base for exploring southern Vermont during fall. Set beside the Retreat Meadow, this beautifully restored 1938 French Baronial manor features six thoughtfully appointed guest rooms, personalized hospitality, and a gourmet breakfast prepared fresh each morning. Guests can even enjoy remarkable foliage from the property, including views of one of the country’s largest Cut Leaf Japanese Maple trees.
Whether you spend your days hiking scenic trails, exploring Vermont’s picturesque byways, or relaxing on the property, Brattleboro offers everything needed for an unforgettable fall in New England. Reserve your stay atthe premier Bed and Breakfast in Brattleboro VT to one of New England’s most beautiful seasons.
Plan an Anniversary Getaway in Southern Vermont
Best Anniversary Getaway Ideas in Southern Vermont
An anniversary getaway in Southern Vermont should feel personal, unrushed, and worth remembering. Brattleboro offers exactly that, combining New England character with a creative, welcoming energy that makes celebrating another year together feel meaningful. For couples searching for anniversary getaway ideas that balance romance, relaxation, and memorable experiences, this corner of Vermont delivers with ease.
There are so many things to do in Brattleboro that invite couples to slow down and enjoy time together. Scenic walking trails wind through town and into the surrounding hills, offering quiet moments without feeling remote. The Retreat Trails are especially popular for early morning or sunset walks, and conversation comes naturally. Downtown Brattleboro adds a lively contrast, with independent bookstores, galleries, and locally owned shops that make wandering feel purposeful and fun. Exploring together becomes part of the celebration rather than an item on a checklist.
Dining plays a central role in any romantic anniversary getaway, and Brattleboro’s food scene consistently impresses. Farm-to-table restaurants and intimate dining rooms create the right atmosphere for marking a milestone, with Peter Havens Restaurant standing out as a favorite for special occasions. Beyond dinner, couples often discover that some of the best anniversary moments happen unexpectedly, whether on a scenic drive through nearby villages, stopping at a covered bridge, or finding a quiet overlook along the way.
Cultural experiences round out the getaway. Live music, theatre, and film screenings reflect Brattleboro’s creative spirit, while tastings at nearby wineries and specialty producers offer a relaxed way to spend an afternoon together. These shared experiences are what transform a simple trip into one of the most rewarding romantic getaways.
Where to Stay for an Anniversary in Southern Vermont
Choosing the right place to stay elevates the entire experience. Inn on Putney Road is a premier Southern Vermont Bed and Breakfast designed with couples in mind. Elegant guest rooms, award-winning gardens, and a daily three-course gourmet breakfast create an atmosphere that feels indulgent without being formal. Personalized anniversary getaway packages add thoughtful touches that let couples focus on each other. For those planning a romantic celebration, it remains one of the most memorable anniversary getaways in Southern Vermont. Book your stay and celebrate your milestone with intention.
See a Show at the Latchis Theater in Vermont
Best Latchis Theater in Downtown Brattleboro for Couples
The Latchis Theater has been the cultural centerpiece of downtown Brattleboro since 1938, offering couples one of the most memorable things to do in Southern Vermont. Built as a “Town Within a Town,” this Art Deco landmark continues to anchor the creative spirit of the region while delivering an elevated night out. From the moment you step inside the Latchis Theater, the experience feels special. Decorative columns, sweeping balconies, rich red velvet seating, and a brilliant blue ceiling adorned with zodiac symbols create a setting that feels cinematic before the show even begins.
Programming is equally impressive. With four theaters and the largest movie screen in Southern Vermont, the Latchis features popular releases, independent films, and timeless classics. Couples also enjoy special broadcasts such as the Met Opera Live in HD, National Theatre productions from Britain, and Exhibition on Screen presentations showcasing the world’s greatest museums. Live concerts, comedy shows, and community performances round out a dynamic calendar that makes this venue one of the top things to do in Brattleboro.
An evening here is the perfect addition to exploring downtown Brattleboro. Browse independent bookstores, enjoy craft cocktails, or reserve a table for a romantic dinner just steps away. Everything is walkable, creating a relaxed yet sophisticated date-night atmosphere.
Stay at a Brattleboro Bed and Breakfast Nearby
After an unforgettable evening at the Latchis Theater, retreat to a refined Brattleboro Bed and Breakfast just minutes from downtown. The Inn on Putney Road offers six luxury guest suites set within a historic mansion surrounded by award-winning gardens. Couples can unwind in beautifully appointed rooms with inviting sitting areas, stroll through private grounds, or access the nearby Retreat Trails directly from the property. In the morning, a gourmet breakfast is always included with your stay.
For couples seeking meaningful things to do in Southern Vermont, combine culture in downtown Brattleboro with an intimate stay designed for connection. Reserve your room and plan your escape today.
Vermont Fall Foliage
Driving the Molly Stark Scenic Byway
If you want one drive that captures everything worth seeing in southern Vermont during fall, take the Molly Stark Scenic Byway. This 40-mile stretch of Route 9 connects Brattleboro to Bennington, running straight through the Green Mountain National Forest with mountain overlooks, covered bridges, and small towns that have barely changed in a century. Locals call it the Molly Stark Trail, named for the wife of Revolutionary War General John Stark. Whether you have two hours or a full day, this byway belongs on your Vermont road trip itinerary.
Start in Brattleboro, where the West and Connecticut Rivers meet at the byway’s eastern end. The town has a walkable downtown, working art galleries, and enough coffee shops and bookstores to fill a morning before you ever get on the road. Give yourself time here. Brattleboro is one of Vermont’s most interesting small towns.
What to See Along Route 9 Vermont
Heading west out of Brattleboro, the byway climbs into the Green Mountain National Forest almost immediately. About 20 minutes in, pull off at Hogback Mountain for a scenic overlook with a hundred-mile view across three states on a clear day. No hiking required.
A few miles past Hogback, Molly Stark State Park sits directly along the route. If you have 90 minutes to spare, the Mount Olga Trail is a moderate 1.7-mile loop that climbs to a fire tower with views of the Green Mountains, the Berkshires, and Mount Monadnock in New Hampshire.
From there, the byway continues to Wilmington, a walkable village with good lunch spots and easy access to Mount Snow. The final stretch toward Bennington passes the Robert Frost Stone House Museum in Shaftsbury, where Frost wrote two of his best-known poems, before ending at the Bennington Battle Monument and the town’s covered bridges.
Peak fall foliage along this stretch of Vermont scenic drives usually hits in the first two weeks of October, when the hardwood forest along Route 9 turns deep red and gold against the mountain overlooks. Late spring is worth considering too. By late May, the Green Mountain National Forest is a saturated green, and the overlooks are nearly empty.
Stay at a Brattleboro Bed and Breakfast Before You Drive
The Inn on Putney Road is a six-room French Baronial-style manor, a short walk from downtown Brattleboro, set on an acre of gardens along the West River with direct access to over 17 miles of hiking trails. Start your morning with a two-course gourmet breakfast made from local Vermont ingredients, then be on Route 9 within ten minutes.
Guest rooms fill quickly during foliage season, so if you’re planning to drive the Molly Stark Scenic Byway when the color peaks, book early. As one of the more established options among Vermont scenic byways for a home base, this Brattleboro Bed and Breakfast puts you close to the route and close to town.
Frequently Asked Questions
What is the Molly Stark Scenic Byway?
It is a 40-mile designated Vermont scenic byway running along Route 9 from Brattleboro to Bennington, passing through the Green Mountain National Forest.
How long does it take to drive the Molly Stark Trail?
The drive itself takes about 90 minutes without stops, though most visitors spend three hours to a full afternoon, including overlooks and short hikes.
What is there to see at Hogback Mountain?
Hogback Mountain has a roadside scenic overlook offering views across three states on a clear day, with no hiking required to reach it.
Are there hiking trails at Molly Stark State Park?
Yes. The Mount Olga Trail is a 1.7-mile moderate loop to a fire tower with views of the Green Mountains, the Berkshires, and Mount Monadnock.
Who was Molly Stark?
Molly Stark was the wife of Revolutionary War General John Stark, and the byway takes its name from her.
Book your stay at the Inn on Putney Road today and make our Brattleboro Bed and Breakfast your base for one of Vermont’s best fall foliage drives.
Why Brattleboro is One of Vermont’s Hiking Bases
Hiking Near Brattleboro VT: A Fall Foliage Trail Guide
If you’re planning a trip built around hiking near Brattleboro VT this fall, you’ve chosen one of the most beautiful spots New England. The hills surrounding town turn deep red, burnt orange, and gold through most of October, and the trail network here means you can leave a quiet country road and be hiking within twenty minutes. Some trails start right in town. Whether you want a short loop before lunch or a summit hike that fills an afternoon, Brattleboro sits at the center of some of the best hiking in Vermont to take in fall foliage.
Five State Parks Worth the Drive
Townshend State Park covers 1,244 acres at the base of Bald Mountain along a bend in the West River. The Bald Mountain Trail climbs through hemlock, sugar maple, and birch to a 1,680-foot summit, a moderate-to-difficult 2.75-mile round trip that takes about three hours. Start mid-morning to catch the best light on the ridge.
Jamaica State Park suits mixed-ability groups. There’s an easy riverside walk, a steeper summit route, and a longer trek to a 125-foot waterfall, so your group can split up and meet back at the car. Nearly a third of its 1,122 acres is hardwood forest, which makes for strong color in early to mid-October.
Lowell Lake State Park offers an easy 3.5-mile loop around the lake, about two hours, passing a Revolutionary War-era cemetery along the way. It’s a good choice for families or anyone easing into hiking in Vermont without giving up the foliage payoff.
Wilgus State Park sits along the Connecticut River. The one-mile Pinnacle Trail climbs to a ridgeline view, and the half-mile Wilgus Nature Trail runs along the river with a wildlife-viewing platform for a slower pace.
For one of the last old-growth hardwood stands in Vermont, drive out to Gifford Woods State Park. Sugar maple, beech, yellow birch, and hemlock that have stood for generations line five trails, from easy brookside loops to longer routes out to a waterfall and overlook.
Things to Do in Brattleboro VT After Your Hike
Once your boots come off, downtown Brattleboro offers plenty for anyone exploring things to do in Brattleboro VT. Independent shops, art galleries, and long-running coffee spots line Main Street, and the Latchis Theater still screens films inside a building dating to the 1930s. It’s a great way to round out a day on the trails.
Where to Stay: Inn on Putney Road
Among Brattleboro Vermont Hotels, Inn on Putney Road puts you closest to the action. Located in French Baronial-style home, built in 1929, backs directly onto the Retreat Trail network, so you can walk before breakfast, then come back to a gourmet breakfast before heading out for the day.
Ask about the Take a Hike picnic package, which includes a fabric-lined picnic backpack to keep, a bottle of wine with glasses and a corkscrew, Vermont spring water, and two catered lunches, so you can head straight to the trailhead without a grocery stop.
Frequently Asked Questions
Where can I go hiking near Brattleboro VT?
Townshend, Jamaica, Lowell Lake, Wilgus, and Gifford Woods State Parks are all within a twenty to forty-five minute drive of downtown Brattleboro, and the Retreat Trail network is accessible directly from town.
What is the best time of year for fall foliage hikes near Brattleboro?
Color typically peaks in early to mid-October, though elevation and tree mix shift the timing slightly from park to park.
Are there easy hikes near Brattleboro VT suitable for families?
Yes. Lowell Lake State Park’s flat 3.5-mile loop and the Wilgus Nature Trail are both good options for a gentler introduction to hiking in Vermont.
Which Brattleboro Vermont hotels are within walking distance of trails?
Inn on Putney Road connects directly to the Retreat Trail network from its backyard and sits a five-minute walk from downtown.
Fall books up fast around here. Check availability at Inn on Putney Road and plan your trailside stay.