The best things to do in Winchendon

Camp Monadnock - A Berea Ministry offers year-round Christian camping right at the foot of Mt. Monadnock, so no long drive, with youth camps like Ascend, Encounter, and Ignite, plus retreats for men, women, and whole families. Expect outdoor adventure, time to breathe, and space to grow closer to God and each other.

From the Jaffrey newsletter, October 21, 2026

Whether your kid lives for tree scrambles or chill waterfront sunsets, Mass Audubon's Wildwood Camp for ages 9 to 17 gets them off screens and into real woods with trails, ropes courses, and archery, plus specialty and family camp options in a safe, inclusive community right over in Rindge on Hubbard Pond.

From the Jaffrey newsletter, October 12, 2026

Carved into the granite foothills of Mount Monadnock, The Shattuck Golf Club delivers that Monadnock drama with bent grass fairways, forest framed holes, and wetlands teeming with wildlife. Challenging but fun, then grab a bite at the Dublin Road Taproom & Eatery or keep the swing going in the golf simulator.

From the Peterborough newsletter, October 16, 2026

Right over the border on Sip Pond, Woodbrook Condominiums is a seasonal, private community where weekends basically plan themselves. Between tennis and pickleball, bocce, horseshoes, a kid-friendly playground and community events, it's a low-key place to actually relax... and maybe finally fix that backhand.

From the Jaffrey newsletter, October 18, 2026

Flat Rock Disc Golf Course threads a tight, technical layout through secluded central Mass woods, built for players who like shot-shaping more than chuck-and-pray. Community-run since 2008, it hosts quirky nighttime Glo rounds and the annual skins-format Ice Bowl in January... perfect for cabin fever.

From the Orange newsletter, October 9, 2026

Gardner Municipal Golf Course has been a local standby since 1936, with 18 holes in excellent shape, smooth greens, and four sets of tees spanning 4,898 to 6,131 yards, Par 71. Warm up on the range and putting green, then refuel at the second-story deck restaurant overlooking the finishing holes.

From the Winchendon newsletter, October 5, 2026

Family owned since 1962, Bowling Acres nails that New England candlepin vibe with glow bowling, leagues and an arcade full of redemption, crane and video games. Grab a lane, then hit the grill for pizzas, burgers, subs and salads, because strikes pair well with fries.

From the Peterborough newsletter, October 10, 2026

Templewood Golf Course is a serene Central Mass escape with lush fairways, challenging greens, and views that make a bogey sting less. Book tee times online, join a league, or line up an event when the crew needs an excuse to swing and hang.

From the Winchendon newsletter, October 29, 2026

Over in Jaffrey, The Park Theatre mixes lovingly restored classics, new family-friendly picks, and small-stage happenings like open mic nights and one-man shows. When you want a low-key night with real community energy, this is the spot that keeps the screen bright and the calendar interesting.

From the Winchendon newsletter, October 31, 2026

If your kid thrives with structure and extra support, Camp Starfish offers truly individualized summer and year-round programs for ages 6 to 17 with a 1:1 staff-to-camper ratio. Choose 5 to 14 day sessions, plus specialty and respite options that keep growth fun.

From the Winchendon newsletter, October 24, 2026

Whether your swing needs tuning or you just want to play a full round without chasing balls, Birdie Train Golf Lounge delivers with a Trackman simulator, 200+ courses and friendly league play. It’s tucked inside The Boiler Bar & Grille, so your tee time pairs nicely with burgers, BBQ and zero weather excuses.

From the Orange newsletter, September 28, 2026

Monadnock Country Club has been part of Peterborough golf for over a century, with memberships for regulars, leagues, private lessons, and venue rentals when a round turns into a celebration. It’s the kind of place where you play, then hang out because you keep seeing friends.

From the Jaffrey newsletter, October 30, 2026

Between gymnastics basics, ninja-style obstacles, and cheer training, Monadnock Gymnastics Center- Ninja, Gymnastics, Cheer gives Peterborough kids a place to move, learn, and burn off the wiggles. It’s a welcoming, skills-first spot that turns couch-cannonballs into cartwheels and confidence.

From the Peterborough newsletter, October 3, 2026

Gardner Ten Pins keeps it classic with 24 lanes, live scoring, and an arcade, plus a bar and grill slinging rotating drafts, mozzarella sticks, and gluten-free pizzas. Join a league, book a lane, or celebrate a birthday and call it a win for North Central MA.

From the Winchendon newsletter, October 20, 2026

Part block party, part art fair, North Quabbin Garlic & Arts Festival brings live music, spoken word, cooking demos, kids activities, and a whole lot of locally grown flavor. Run by neighbors, for neighbors, it’s the weekend you catch up with half of town and discover your new favorite farm or artist.

From the Orange newsletter, September 27, 2026

When your clubs are begging for fresh air, Ellinwood Country Club is a friendly, well-kept spot locals actually use, with public tee times, active leagues, and a clubhouse that doubles for celebrations. Play a quick nine after work or make a day of it with friends.

From the Orange newsletter, September 26, 2026

, operating since 1959, takes you to 14,000 feet for tandem jumps or to learn to skydive solo, with views of the Appalachian Mountains and even the Boston skyline... just up the road in Orange. Perfect if your weekend needs a little more "whoa".

From the Athol newsletter, September 23, 2026

New Hampshire's oldest movie theater, Peterborough Community Theatre keeps things delightfully old-fashioned with no advance tickets, just show up and enjoy a rotating slate of crowd-pleasers, plus that cozy small-town energy that makes catching a flick feel like an event, not an errand.

From the Jaffrey newsletter, October 24, 2026

Franklin Park Zoo is your go-to when the week needs a nature break, with the indoor Tropical Forest, kid-pleasing Children’s Zoo, playful Nature’s Neighborhoods, Franklin Farm, and the seasonal Butterfly Oasis, plus real conservation work that makes each visit feel good for you and the planet.

From the Boston newsletter, October 8, 2026

When the week is doing the most, take the elevator up to View Boston for 360° views, breezy indoor-outdoor decks, and the new Summer Reimagined exhibits that turn the city into a giant, interactive cheat sheet. Cap it with a cocktail at Stratus Rooftop Bar and remember why you live here.

From the Boston newsletter, October 15, 2026

Roadrunner keeps concerts easy with a clean, roomy floor, a tiered balcony for actually seeing the stage, and multiple bars so your intermission sprint is optional. Check the calendar for this week, grab a friend, and make a midweek show feel like a small victory.

From the Boston newsletter, October 1, 2026

If your short game and social life need a lift, Oak Hill Country Club brings a brilliantly designed, impeccably kept course, multiple dining spots, tennis, swimming and an expansive patio for unwinding. Membership is open, and the member community is the real secret sauce.

From the Leominster newsletter, August 19, 2026

Fenway Park has 100+ years of stories, the small-capacity buzz locals love, and yes, the occasional big-name concert. Home of the Red Sox, it’s perfect for a last-minute game or a ballpark tour when you want a dose of real-deal Boston.

From the Brookline newsletter, October 30, 2026

With roots back to 1908, Monoosnock Country Club is your close-to-home spot to book a tee time, sharpen the short game with lessons, then refuel at Grille 19. Bonus, the pro shop has you covered and the function space keeps celebrations on the fairway vibe.

From the Leominster newsletter, October 15, 2026

Underground at Ink Block turns the space beneath the overpass into Boston's urban playground, with 21 jaw-dropping murals curated by Street Theory, a free first-come pickleball court, a dog area, skate park, bike paths, and events. Perfect quick creative recharge when Waltham feels routine.

From the Boston newsletter, September 13, 2026

When the kids are climbing the walls, BB Kidz Klub brings bounce houses, arcade games, and Lego tables so you don't have to rearrange your living room. Swing by for open play or hand off birthday planning to their crew, then accept the hero status you clearly deserve.

From the Leominster newsletter, October 28, 2026

Athol Cinemas 8 has leather recliners, reserved seating, and classic concessions so you can actually enjoy the movie, not just endure it. First-run flicks and even birthday or private rentals make it a solid go-to when Orange needs a no-fuss night out.

From the Orange newsletter, September 25, 2026

Swap the same-old plans for Puttshack Boston, where tech-infused mini golf means balls that keep score, interactive challenges, and plenty of friendly trash talk. Grab shareable bites and craft cocktails between holes and make it a Seaport date night or crew hang that actually delivers.

From the Boston newsletter, September 24, 2026

Craving a mini escape that doesn't involve a long drive? Simons Theatre at the New England Aquarium throws you into 3D ocean adventures on a giant screen nearly five stories high, with Penguins: A Love Story, Sea Otters: A Wild Family Adventure, and Ocean Dreams bringing big feels and bigger visuals.

From the Boston newsletter, October 22, 2026

Entertainment Luxury Cinemas Leominster is the outpost of a local chain bringing new releases to a cozy, old-fashioned setting. Ideal for date night or a midweek escape, it delivers that simple, hometown movie experience that just works, no fuss and all the popcorn.

From the Leominster newsletter, October 31, 2026

Gardner Cinemas keeps the big-screen outing refreshingly simple, with clean recliner seats, classic snacks, and arcade games for a little pre-show fun. Check out what’s playing, pick your seat, and settle in for an easy local escape that doesn’t require a complicated plot.

From the Worcester County newsletter, October 29, 2026

J. 0, including an award-winning favorite that earned Room Escape Artist’s Golden Lock-In back in 2018.

From the Leominster newsletter, October 12, 2026

Putt Across America turns a quick Boston outing into a coast-to-coast 18-hole journey through iconic landmarks, from roaring waterfalls to Bourbon Street to a lucky spin on the Vegas strip. It's indoors, bright, photo-friendly, and perfect for birthdays, group hangs, or an easy night of friendly trash talk.

From the Boston newsletter, October 29, 2026