Chesterfield, NH — Monadnock Region
16 minutes to Keene NH · 16 minutes to Brattleboro VT · 2 hours from Boston
Golf, arts, history, farms, and family fun — all within a short drive.
Est. 1900 — a 9-hole course just down the street with very good greens. Old-fashioned New England golf at its finest. Don’t be fooled by the short yardage; hole #3 is the toughest par 5 you’ll ever play.
A hidden gem usually in very good condition, with great views, a pro shop, and an excellent Italian restaurant at the course for lunch or dinner.
Rated by Golf Magazine (2020) as one of the best stand-alone 9-hole golf courses in the world.
36 holes described as “one of the country’s great public golf courses — big, bold, beautiful, and fair.” Four sets of tees. Excellent snack bar. Call ahead for a tee time.
A top-notch course that has hosted many professional and amateur tournaments. Sister course to Fox Hopyard in CT.
Located at the base of Mt. Monadnock. Rated the most difficult course in all of New England. Spectacular views. Bring extra golf balls. Stop at Kimball Farms for ice cream after.
A nonprofit working farm offering tours, recreation trails, visiting farm animals, a farm store, hay and sleigh rides, and seasonal events. 242 Chesterfield Rd, Keene.
Family-owned restaurant and ice cream parlor on RT 63 with great views of Spofford Lake along the way. Summer cruise nights with classic cars, kids’ play area, and outdoor dining. Certified organic sugar house shipping pure NH maple syrup worldwide.
Americana at its best. Collegiate wooden bat baseball in the NECBL — many major leaguers got their start here. Family oriented, inexpensive tickets, autographs galore. Alumni Field on Arch Street.
Apple, blueberry, and peach picking at this you-pick orchard. Beautiful hill views, a small pond, and roaming cows. Frequent family events.
A clean, state-of-the-art indoor rink at 380 Marlboro St. Quality skate rentals, affordable public skate. A hidden jewel.
Take private glass blowing lessons and choose from a variety of items to make.
Feed and interact with animals — a classic New England family outing.
A stunning greenhouse filled with gardens, live butterflies, and hidden creatures. Fun for the whole family.
Est. 1924. A nonprofit downtown theatre hosting independent films, live music, comedy, and drama. Amelia Earhart once lectured here on cross-Atlantic air travel.
A Greco-Deco gem built in 1938, bedecked with Hungarian murals and a panoramic Zodiac ceiling. Current cinema and eclectic live events.
A fully furnished historic New England home, free to visit at 199 Main Street in scenic downtown Keene.
Both downtowns are worth a visit and very different in feel. Keene is quintessential New England — the widest paved main street in the world (172 ft) anchored by the iconic 1737 UCC Church. Brattleboro is eclectic — locally owned shops, breweries, artisans, galleries, and the historic Latchis Theatre overlooking the Connecticut River.
Walk through an authentic 18th-century colonial New England village. Twelve preserved antique houses (1730–1850) with world-class regional furniture, silver, and textiles.
Saturdays 9am–12pm, June through October, in the Center of Chesterfield on Rt 63. Fresh local produce with views of the Green Mountains.
An all-growers market open Saturdays 9am–1pm and Tuesdays 3–6pm, late April through October. Live music, wide variety of vendors. Commercial Street parking lot off Gilbo Avenue.
Saturday market 10am–2pm, May–October at 570 Western Ave. Tuesday market downtown at New England Youth Theater. Don’t miss Bread from the Earth sourdough.
Monadnock Food Co-op at 34 Cypress St in downtown Keene, and Brattleboro Food Co-op at 2 Main St downtown Brattleboro.
From a wooded island in the middle of the lake to the world’s most-hiked mountain — all within reach.
A beautiful 5-acre wooded island right in the middle of Spofford Lake. Kayak or boat to it from the dock to swim and hike. Home to Native American relics and paleo-Indians over 10,000 years ago.
A geologic park with a quick, picturesque hike right in the neighborhood. A must-do. Located on the north side of Rt. 9 across from Wellington Dr. on the way into Keene.
Walk the “staircase to nowhere” and see the ruins of Madame Sherri’s castle — one of NH’s most eccentric residents known for lavish roaring-twenties parties. The forest connects to Mt. Wantastiquet and Pisgah State Park for longer journeys.
A 42-mile multi-use trail running through Fitzwilliam, Troy, Keene, Westmoreland, and North Walpole along 1700s rail beds. Great for walking, running, cycling, and dog-walking. Closest access off Rt 9 on Whitcombs Mill Road.
Beautiful forest park with trails for all levels — swim at Kilburn Pond in summer, snowshoe the Pisgah Ridge for sunrise views in winter. Kilburn Parking lot on Rt 63, south of the Chesterfield line.
Moderate trails, the preserved Colony home, and the original foundation. Trailhead on Daniels Hill Road in Keene — take Rt 9 east, right on Daniels Hill Rd, parking lot 1/8 mile on left.
Beautiful views of the Connecticut River Valley and Brattleboro. A trail connects with Madame Sherri Forest for a longer route.
Multiple trails to adjust length and difficulty. Beautiful views of Mt. Monadnock and the Green Mountains.
The most frequently climbed mountain in the world. Day passes can be scheduled at the park. A classic New Hampshire experience.
A 2–3 hour intermediate hike with views of Haystack Pond, Mt. Pisgah, and Harriman Reservoir. Wildflowers in spring and summer.
“Vermont’s Little Grand Canyon” — hike the gorge trail, fish, and enjoy nature programs. Remnants of an 1836 wool mill visible at the head of the gorge.
Innumerable trails for all levels. The Kancamagus Scenic Byway offers swimming in the Swift River, scenic lookouts, and trail options for all abilities. The Appalachian Trail passes through. Be sure to visit the Basin and Flume.
Skating on the lake, Nordic trails, and some of New England’s best ski mountains — all within reach.
Bring your ice skates and skate right on the lake. Stay warm at the beach fire pit.
Volunteer-operated ski hill — small, affordable, family-friendly with a minimal snack bar.
Tubing, cross-country skiing, downhill skiing, and snowboarding. Equipment rentals and a snack shack.
25 miles of scenic cross-country trails, 6 miles maintained for snowshoeing. Rentals and food at the base yurt.
Downhill skiing, snowboarding, tubing, terrain parks, spa, childcare, and several dining options.
Downhill skiing, snowboarding, and tubing. Also open in summer with a bike park, white water rafting, and zipline canopy tours.
Largest snowmaking system in NH. Skiing, snowboarding, snowshoeing, and tubing. Onsite pub.
Naturally narrow, Swiss-inspired trails descending 1,500 vertical feet. Boundary-to-boundary tree skiing. True old-school New England skiing.
The highest peak in Southern Vermont — 99 trails, Nordic skiing, ice skating, snowshoeing, fat bikes, tubing, and multiple dining options at Stratton Village.
Nordic and downhill skiing, snowboarding, spa, and an indoor golf training center.
New England’s largest ski resort — downhill skiing, snowboarding, rentals, and several dining options.
Keene’s vibrant downtown has something for every taste.
Right in the center of Keene at the head of the square. Known for unique fine dining, rich desserts, and cocktails. Where presidential candidates eat every 4 years.
Funky fine dining with a craft cocktail bar, eclectic art, and seasonal small plates. Great for exploring multiple dishes over cocktails. Vegan, vegetarian, and gluten-free options.
The “Cheers” of Keene. Family-style comfort food, great BBQ, seafood, and Italian. Very reasonably priced and relaxed.
Known for fabulous authentic Thai food with a range of spice levels. Vegetarian/vegan options. Their pad Thai is a must-try.
Hip taco joint with fusion tacos, burritos, and rice bowls. Small establishment, perfect for grab-and-go lunch or dinner.
Pho, unique cocktails, and American fusion options. Vegan, gluten-free, and vegetarian friendly.
Comforting Mediterranean-Italian cuisine in a casual atmosphere with diner booths and a stone-walled bar. Wood-fired pizzas.
Authentic Jamaican food in downtown Keene.
Brick oven pizza, specialty pies, and Sunday brunch. Locations in both Keene and Brattleboro.
Coffee shop in downtown Keene with a rotating selection of pastries and snacks.
Bagels, bread, baked goods, smoothies, grain bowls, and sandwiches. Locations in Keene and Brattleboro. Vegan/vegetarian options.
Plant-based café inside the Toad Stool Bookshop downtown. Mostly organic/non-GMO ingredients. Rotating gluten-free desserts. Enjoyed by plant-based and non-plant-based eaters alike.
Eclectic, locally-owned, and farm-forward. Brattleboro punches well above its size for dining.
Dinner in a restored 1925 Worcester Dining Car. Menu features local, organic ingredients and changes daily. A Brattleboro institution.
Casual eatery on the water with beautiful views and sunsets. Seafood, burgers, steaks, pasta, and house-made desserts. Sunday brunch buffet with live jazz guitar. Kayak and canoe rentals available.
Casual farm-to-table with seasonal New American cuisine and weekend brunch.
Fermented since 2014 with only wild Brattleboro mixed-culture yeast in a wood-fueled brewhouse.
Craft beer and pub fare in a fire-lit dining room sitting directly on the Vermont/New Hampshire boundary line, with a beautiful view of the Connecticut River.
Brick-oven pizzas and creative Italian fare in stylish surrounds on Main Street.
Specializes in house-made Italian pasta with a rotating menu.
Awarded “Best Vegetarian Cuisine” by Yankee Magazine (2017). Seasonal, organic plant-based cuisine from elixirs and raw foods to full brunch, lunch, and dinner.
Award-winning BBQ served through a quick-serve window. A Brattleboro staple.
Tastings, cocktails, events, and food trucks. Check their website for seasonal hours.
Brick oven pizza, specialty pies, and Sunday brunch. Locations in both Brattleboro and Keene.
Family-operated restaurant serving authentic Mexican and Mayan foods inspired by recipes passed down through generations.
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