Things to Do & Places to See

One of the best parts of staying here is discovering the little gems nearby. We’ve put together a collection of favorite hikes, towns, food stops, and experiences to help you explore like a local. Tap any photo to dive in.

Local Farmer's Markets

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Hartland Farmers Market

Approx. 5 miles
When: Fridays, 4:00–6:30 PM (seasonal, typically late May–early Sept)

A small, friendly community market featuring local produce, baked goods, meats, flowers, and handmade items.
Website

Norwich Farmers’ Market

Approx. 18–19 miles
When: Saturdays, 9:00 AM–1:00 PM (May–October)
https://www.norwichfarmersmarket.org/

One of the Upper Valley’s largest and most well-known markets, with excellent produce, baked goods, meats, and artisan vendors. Winter indoor markets are also offered seasonally. Close to King Arthur Flour.
Website

Windsor Farmers’ Market

Approx. 6–8 miles
When: Sundays, 11:30 AM–2:30 PM (June–October)
Info page:
https://www.vtfarmtoplate.com/food-system-map/windsor-farmers-market

Held on the Windsor Village Green with local food, crafts, and seasonal produce.

Lebanon Farmers’ Market (Colburn Park, NH)

Approx. 15–19 miles
When: Thursdays, 4:00–7:00 PM (mid-May–late Sept)
https://lebanonnh.gov/806/Farmers-Market

A lively market in downtown Lebanon with food trucks, local farms, and live music.

Market on the Green (Woodstock)

Approx. 5 miles
When: Wednesdays, 3:00–6:00 PM (summer–early fall)
https://www.woodstockvt.com/event/market-on-the-green/

A classic Vermont farmers’ market on Woodstock’s village green with food vendors, live music, and a great small-town atmosphere.

Local Swimming Near Stillwood

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North Hartland Lake (Beach & Swim Area)

Approx. 8–10 miles
Type: Sandy beach + swimming area on Ottauquechee River reservoir
When: Daylight hours; summer swimming & picnics
Info:
https://www.recreation.gov/camping/campgrounds/251044

A classic summer favorite with a sandy swimming beach, picnic tables, and plenty of space to relax by the water.

Kedron Valley Inn Pond – South Woodstock

Approx. ~5 miles
Type: Private pond with sandy beach & swim dock
When: Summer (passes available)
Info:
https://www.woodstockvt.com/locals-guide-summer-swimming-holes-in-woodstock/
Additional pass info available locally at the South Woodstock Country Store.

A spring-fed pond with a sandy beach and small swim dock — gentle water and grassy lawn areas make this a great family spot.

Martin Mill Covered Bridge (Lulls Brook) – Hartland, VT

Approx. 6–7 miles
Type: River swimming hole
When: Daylight hours; best in summer during lower water levels
Directions:
Park on the south side of Martin Mill Covered Bridge on Martinsville Road (about ½ mile from Hartland Elementary School). Follow the steep footpath over the old mill foundations down to Lulls Brook.
Info:

A tucked-away swimming hole below Martins Mill Covered Bridge. A steep path leads down to Lulls Brook (use caution). Roaring water over rocks, a still pool about five feet deep, shallow soaking spots, and a sunny bank on the far side.

Pompanoosuc Mills / Ompompanoosuc River – Norwich/Thetford line

Approx. 20–22 miles
Type: River swimming hole
Info:
https://vnews.com/2016/07/22/summer-guide-upper-valley-swimming-holes-2637291/

A classic Upper Valley river swim with deeper pools and rocky access. Not formal or maintained — very much a local favorite.

Kennedy Pond – Windsor Recreation Pond

Approx. ~8 miles
Type: Public pond swim & play area
When: Typically open in warmer months; check Windsor Recreation for exact seasonal hours
Info:
https://windsorvt.myrec.com/info/facilities/details.aspx?FacilityID=14698

A local pond swimming and recreation area managed by Windsor Recreation — great for casual swims and family time.

Quechee Gorge Swimming / River Access

Approx. ~10 miles
Type: Gorge river swimming
Info:
https://www.woodstockvt.com/locals-guide-summer-swimming-holes-in-woodstock/
https://vtstateparks.com/quechee.html

Hike down to the Ottauquechee River below the Quechee Gorge Bridge for a cool, scenic swim.

Ayers Brook Swimming Hole – Randolph, VT

Approx. 30 miles
Type: River swimming hole with cascades
Info:
https://vnews.com/2016/07/22/summer-guide-upper-valley-swimming-holes-2637291/

A beautiful swimming hole with small waterfalls and deep pools along Ayers Brook. A favorite on hot days, though access requires a short walk and careful footing.

Storrs Pond Recreation Area – Hanover, NH

Approx. 20 miles
Type: Managed pond with beach & facilities
When: Seasonal, staffed beach during summer
Website:
https://www.hanovernh.org/263/Storrs-Pond-Recreation-Area

A well-loved Upper Valley swimming spot with sandy beach, lifeguards, restrooms, and picnic areas. Great for families and guests who want an easy, safe swim.

Mascoma River Greenway Access Points – Lebanon, NH

Approx. 18–20 miles
Type: River swimming & wading
Info:
https://vnews.com/2016/07/22/summer-guide-upper-valley-swimming-holes-2637291/

Several informal access points along the Mascoma River where locals wade and swim during hot spells. Water levels can change quickly after rain.

Ottauquechee River – Woodstock Village Spots

Approx. ~6 miles
Type: River swimming & wading
Info:
https://www.woodstockvt.com/locals-guide-summer-swimming-holes-in-woodstock/

The Ottauquechee flows through Woodstock with a few easy access points:
• At the Lawn of the Woodstock History Center — shallow wading and swimming with views of the Middle Covered Bridge.
• Between the Recreation Center and Little Theater — family-friendly sandy riverbank and waist-deep swimming.

Silver Lake State Park – Barnard, VT

Approx. ~16 miles
Type: Lake beach with amenities
When: Seasonal with parking/entry fees
Info:
https://www.vtstateparks.com/parks/silver-lake

A well-appointed lake beach with sandy shore, picnic tables, snack bar, playground, and facilities — more “beach day” than remote swim spot.

Cedar Circle Farm / White River Access – East Thetford, VT

Approx. 17–18 miles
Type: River swimming & wading
Info:
https://vnews.com/2016/07/22/summer-guide-upper-valley-swimming-holes-2637291/

Swimming access along the White River near East Thetford, often used by locals for cooling off after hot days. Conditions vary by water level.

Union Village Dam / Ompompanoosuc River – Thetford, VT

Approx. 22 miles
Type: River & dam swimming area
Info:
https://vnews.com/2016/07/22/summer-guide-upper-valley-swimming-holes-2637291/

A broad swimming area with calmer water near the dam, popular with locals. Best during lower water levels and warm weather.

Boston Lot / Boston Pond (Lebanon, NH)

Approx. 16–18 miles
Type: Natural pond / conservation area
When: Daylight hours; summer swimming
https://www.lebanonnh.gov/1249/Boston-Lot

Boston Pond is located within the Boston Lot, a large conserved forest area just outside downtown Lebanon. The pond is peaceful and scenic, with informal access for swimming on warm days. A great choice for guests who enjoy quieter, more natural spots paired with a walk in the woods.

Take advantage of leash-optional hikes right from the property, which hooks up to the VAST trail, or explore some of the local hikes just a short drive away.

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Mt. Ascutney – Windsor, VT

Approx. 6–7 miles
Difficulty: Moderate to strenuous (depending on route)
Trail info:
https://www.vtstateparks.com/ascutney.html

A local classic with multiple trail options ranging from steady climbs to steeper ascents. Rewarding views from the summit and great exercise for energetic dogs. Trails can be rocky in places.

Hartland Winter Trails – Hartland, VT

Approx. 5 miles
Difficulty: Easy to moderate
Leash required: Recommended
Trail info:
https://hartlandwintertrails.org/

A local gem with a mix of forested trails and open fields. These trails are used year-round and are great for casual walks, snowshoeing, X-country skiing, and mellow outings with dogs.

Mt. Peg – Woodstock, VT

Approx. 5 miles
Difficulty: Easy to moderate
Trail info:
https://www.woodstockvt.com/mount-peg/

A wonderful network of wooded trails just outside Woodstock village. Ideal for dogs, with gentle grades, loops of varying lengths, and scenic overlooks. One of the most popular local dog walks.

Quechee Gorge Trails – Quechee, VT

Approx. 18 miles
Difficulty: Easy to moderate
Leash required: Yes
Trail info:
https://vtstateparks.com/quechee.html

Short scenic hikes with dramatic views of the gorge. Dogs are welcome on leash. Some sections are steep or rocky, so good footing (for humans and dogs) is important.

Mt. Tom – Woodstock, VT

Approx. 6 miles
Difficulty: Easy to Moderate
Trail info:
https://www.nps.gov/mabi/planyourvisit/mount-tom.htm

Part of the Marsh-Billings-Rockefeller National Historical Park, Mt. Tom offers carriage roads and forest trails with lovely views over Woodstock. Well-maintained and perfect for leashed dogs.

Mount Cube – Orford, NH

Approx. 23 miles
Difficulty: Moderate to strenuous
Leash required: Yes
Trail info:
https://www.trails.org/our-trails/mount-cube/

A favorite Upper Valley hike with rewarding summit views. A bit farther, but worth it for guests looking for a more challenging adventure with their dog.

Kayaking & SUPing Near Stillwood

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North Hartland Lake (Hartland Dam)

Approx. 8 miles
Type: Calm lake paddling (kayak & SUP)
When: Daylight hours; best late spring–early fall
Info:
https://www.nae.usace.army.mil/Missions/Recreation/North-Hartland-Lake/

A favorite local spot for relaxed paddling. Calm water makes this ideal for beginners, SUPs, and peaceful evening kayaks. Scenic, quiet, and rarely crowded.

Kennedy Pond – Windsor, VT

Approx. 7–8 miles
Type: Small pond paddling
When: Seasonal; daylight hours
Info:
https://windsorvt.myrec.com/info/facilities/details.aspx?FacilityID=14698

A mellow local pond managed by Windsor Recreation. Best for short kayak or SUP outings and calm-water paddling.

Grafton Ponds State Park – Grafton, VT

Approx. 35–40 miles
Type: Lake paddling (kayak & SUP)
When: Daylight hours; best late spring through fall
Directions:
Access via Grafton Ponds State Park; parking and lake access are clearly marked once inside the park.
Info:
https://vtstateparks.com/grafton.html

A much-loved Vermont paddling destination with clear water, peaceful surroundings, and plenty of space for kayaking and paddleboarding. Early mornings are especially calm and beautiful. Seasonal parking fees apply.

Connecticut River – Windsor / Hartland area

Approx. 6–10 miles (various access points)
Type: Flatwater river paddling
When: Best during summer and low-flow periods
Access info:
https://www.greatriveroutfitters.com/river-trip

A classic Upper Valley paddling experience. Long, gentle stretches are perfect for kayaking and SUP when water levels are moderate.

Mascoma Lake – Lebanon, NH

Approx. 16–18 miles
Type: Lake paddling
When: Summer season; daylight hours
Info:
https://www.lebanonnh.gov/1108/Mascoma-Lake

A larger lake with plenty of space for kayaking and paddleboarding. Early mornings and evenings are best for calmer water.

Ottauquechee River – Woodstock, VT

Approx. 15–16 miles
Type: River paddling (conditions vary)
When: After calm weather; water-level dependent
Info:
https://www.woodstockvt.com/parks-and-recreation/

A scenic river for experienced paddlers during appropriate water conditions. Some sections are better for short floats than long paddles.

White River – WRJ/Royalton / Bethel area

Approx. 8–18 miles
Type: River kayaking
When: Water-level dependent; spring & early summer best
Info:
https://www.americanwhitewater.org/content/River/view/river-detail/1320/main

More dynamic river paddling with sections suited to experienced kayakers. Conditions vary greatly—check levels before heading out.

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Hartland Winter Trails

Approx. 3 miles
When: Year-round (conditions permitting)

A network of gentle woodland trails perfect for walking, snowshoeing, fat biking, and easy family adventures. Free and great for all ages.

https://hartlandwintertrails.org/

Ottauquechee River (Hartland Access Points)

Approx. 3–6 miles
When: Late spring–early fall (weather dependent)

Shallow, slow-moving sections of river ideal for wading, skipping stones, and exploring along the banks. Great supervised summer fun for kids.

Hartland Recreation Area

Approx. 5 miles
When: Open daily

A local favorite with playground equipment, open fields, and space to run and play. An easy stop to burn off energy close to home.

https://hartlandvt.myrec.com/info/default.aspx

Hartland Farmers Market

Approx. 5 miles
When: Fridays, 4:00–6:30 PM (seasonal, typically late May–early Sept)

A small, friendly community market featuring local produce, baked goods, meats, flowers, and handmade items.

https://hartlandfarmersmarket.com/

Wellwood Orchards

📍 Springfield, VT
Approx. 20 miles
When: September–October

A classic Vermont apple orchard with pick-your-own apples, cider donuts, hayrides, and a large farm store. A fun fall outing for all ages.
https://wellwoodorchards.com/

Quechee Gorge Village Tubing Hill

📍 Quechee, VT
Approx. 9 miles
When: Winter (conditions permitting)

A popular family tubing hill with lift service, making it easy for kids (and parents). Conveniently located near shops and food.

Ascutney Outdoors

📍 West Windsor, VT
Approx. 25 miles
When: Year-round (activities vary by season)

A community-run outdoor recreation area offering hiking and mountain biking in warmer months, and sledding, snowshoeing, backcountry skiing, and community events in winter. Family-friendly, low-key, and a great option for kids who like being outdoors without the crowds of a large resort.

https://www.ascutneyoutdoors.org/

Billings Farm & Museum

📍 Woodstock, VT

Approx. 6 miles
When: Open daily (seasonal hours vary)

A hands-on working dairy farm with animals, historic barns, kid-friendly exhibits, and seasonal activities. A favorite for younger children.
https://billingsfarm.org/

Marsh–Billings–Rockefeller National Historical Park

📍 Woodstock, VT

Approx. 6 miles
When: Open daily (visitor center seasonal)

Wide, stroller-friendly carriage roads and forest trails, plus a visitor center with interactive exhibits about land stewardship and conservation.

Woodstock Village Green

📍 Woodstock, VT

Approx. 6 miles
When: Year-round

An open green in the heart of Woodstock where kids can run around while adults enjoy nearby shops, cafés, and seasonal events. Farmer's Market & live music on Wednesday afternoons in the warmer months.

Games Room at the Woodstock Inn

📍 Woodstock, VT

Approx. 6 miles
When: Daily

An indoor game room featuring classic arcade games, air hockey, and other activities—perfect for rainy or cold days with kids.

Sugarbush Farm

📍 Woodstock, VT
Approx. 7 miles
When: Year-round (sugaring season peaks March–early April)

A working maple farm offering free syrup samples, farm animals, scenic views, and a small shop. Very kid-friendly and close by.

https://sugarbushfarm.com/



Quechee Gorge

Approx. 9 miles
When: Year-round

Vermont’s most famous natural attraction, with dramatic views, short walking paths, and river scenery below. Older kids especially enjoy the bridge and overlooks.
https://www.hartfordvtchamber.com/quechee-gorge-visitor-center/

Montshire Museum of Science

📍 Norwich, VT

Approx. 18 miles
When: Open daily (hours vary)

A hands-on science museum designed for kids, with interactive indoor exhibits and an outdoor water play area in warmer months. A rainy-day standout.

https://montshire.org/

Upper Valley Aquatic Center

📍White River Junction, VT

Approx. 10 miles
When: Year-round (schedule varies)

An indoor pool and splash area offering family swim times—great for winter days or bad weather.
https://www.uvacswim.org/

Cedar Circle Farm & Education Center

📍 East Thetford, VT
Approx. 30 miles
When: September–October

A family-friendly organic farm offering apple picking, walking paths, farm animals, and a farm stand with baked goods and cider. Easy and relaxed for kids.
https://cedarcirclefarm.org/

Woodstock Inn Sledding Hill (Mount Peg Area)

📍 Woodstock, VT
Approx. 6 miles
When: Winter, after snowfall

A gentle, well-loved sledding hill near the Woodstock Inn, ideal for younger children and families. Ask at the Inn for current access and conditions.
https://www.woodstockinn.com/sledding-tubing

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Saskadena Six (formerly Suicide Six)

Approx. 9 miles
Type: Alpine skiing & snowboarding
When: Winter season; weather-dependent
Info:
https://www.saskadenasix.com/

A beloved local ski area with a friendly, low-key vibe. Great for beginners, families, and anyone who prefers classic New England skiing without the crowds. Night skiing and lessons available.

Ascutney Outdoors – Brownsville, VT

Approx. 6–7 miles
Type: Alpine skiing, backcountry skiing & snowboarding
When: Winter season; weather- and volunteer-dependent
Info:
https://ascutneyoutdoors.org/

Yes — Ascutney does ski. Formerly Ascutney Mountain Resort, it’s now community-run. Expect a rustic, low-key experience with limited lift service, backcountry options, and occasional events. Best for adventurous skiers and riders who love local character.

Quechee Club Ski Hill – Quechee, VT

Approx. 12–13 miles
Type: Small alpine ski hill
When: Winter season; limited hours
Info:
https://quecheeclub.com/ski-hill/

A small, charming ski hill primarily for Quechee Club members and guests. Best for beginners and kids. Limited public access — worth noting for guests staying nearby or visiting members.

Killington Resort – Killington, VT

Approx. 27–28 miles
Type: Large alpine ski & snowboard resort
When: Winter season (often the longest in the East)
Info:
https://www.killington.com/

Vermont’s largest ski area with extensive terrain for all abilities, terrain parks, and a lively après-ski scene. Great for guests looking for a full-scale resort experience.

Mount Sunapee – Sunapee, NH

Approx. 35 miles
Type: Alpine skiing & snowboarding
When: Winter season
Info:
https://www.mountsunapee.com/

A popular NH resort with lake views, reliable snowmaking, and well-balanced terrain for all abilities.

Pico Mountain – Mendon, VT

Approx. 28–29 miles
Type: Alpine skiing & snowboarding
When: Winter season
Info:
https://www.picomountain.com/

A quieter alternative to Killington with classic Vermont vibes and excellent intermediate terrain. Often less crowded and more relaxed.

Okemo Mountain Resort – Ludlow, VT

Approx. 32–34 miles
Type: Large alpine ski & snowboard resort
When: Winter season
Info:
https://www.okemo.com/

A polished, family-friendly resort known for grooming, snowmaking, and a full village setup. Great for mixed-ability groups.

Dartmouth Skiway – Lyme, NH

Approx. 34–36 miles
Type: Alpine skiing & snowboarding
When: Winter season
Info:
https://sites.dartmouth.edu/skiway/

A no-frills, uncrowded ski hill run by Dartmouth College. Affordable, straightforward, and very local-feeling.

Cross-Country Skiing & Snowshoeing Near Stillwood

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Hartland Winter Trails – Hartland, VT

Approx. 5 miles
Type: Groomed & ungroomed Nordic skiing + snowshoeing
Cost: Free (donations welcome)
Info:
https://hartlandwintertrails.org/

A wonderful local trail network maintained by volunteers. Trails wind through woods and open fields and are perfect for both classic skiing and snowshoeing. A true community gem and one of the closest options to Stillwood.

Woodstock Inn Nordic Center – Woodstock, VT

Approx. 5 miles
Type: Groomed cross-country skiing & snowshoeing
Cost: Day passes required
Info:
https://www.woodstockinn.com/activities/nordic-center/

One of Vermont’s premier Nordic centers, offering beautifully groomed trails, varied terrain, and equipment rentals. Excellent option for guests wanting a polished, full-service experience.

Ascutney Outdoors – Brownsville, VT

Approx. 6–7 miles
Type: Backcountry skiing & snowshoeing
Cost: Free / donation-based
Info:
https://ascutneyoutdoors.org/

Formerly Ascutney Mountain Resort, now a community-run outdoor recreation area. Offers ungroomed routes ideal for adventurous snowshoers and backcountry skiers looking for elevation and quiet trails.

Mount Peg Trail System – Woodstock, VT

Approx. 5 miles
Type: Ungroomed winter hiking & snowshoeing
Cost: Free
Info:
https://www.woodstockvt.com/mount-peg/

A popular year-round trail system that’s equally lovely in winter. Best for snowshoeing or casual backcountry skiing after fresh snowfall.

Dartmouth Skiway Nordic – Lyme, NH

Approx. 34–36 miles
Type: Groomed Nordic skiing
Cost: Day passes
Info:
https://sites.dartmouth.edu/skiway/nordic-skiing/

A quieter Nordic option connected to the Dartmouth Skiway, offering groomed trails and a relaxed atmosphere.

Quechee Lakes Trail System – Quechee, VT

Approx. 12–13 miles
Type: Groomed Nordic skiing & snowshoeing
Cost: Day passes available
Info:
https://www.quecheelakes.com/activities/winter-activities/

A well-maintained trail network with scenic wooded loops and gentle terrain. Great for casual outings and mixed-ability groups. Access typically requires a pass or guest access.

Marsh-Billings-Rockefeller National Historical Park – Woodstock, VT

Approx. 6 miles
Type: Carriage roads for skiing & snowshoeing
Cost: Free
Info:
https://www.nps.gov/mabi/planyourvisit/winter.htm

Wide carriage roads make this an excellent spot for classic skiing and snowshoeing, especially for beginners or those wanting gentle grades and scenic views.

Ready to plan your stay?