Charlton

Day Trips

Make the most of your day with our curated plans, packed with Charlton's hidden gems and unique experiences!

day 1
Arrival and Main Street Welcome
morning
:

Start your morning by arriving in Charlton and settling into your charming local bed and breakfast. Stroll along Main Street to admire historic storefronts that date back to the 19th century. Grab a freshly brewed coffee and locally baked pastry at a family-run café to fuel your first day.

afternoon
:

Head to the Charlton Historical Society to learn about the town’s rich heritage and see rotating exhibits on early settlers and industry. Walk through nearby neighborhoods to marvel at well-preserved colonial and Victorian homes. Stop by a local deli for a hearty sandwich before you continue exploring.

evening
:

Choose a cozy tavern for dinner, sampling regional specialties made with farm-fresh ingredients. Unwind with live acoustic music or a friendly game of darts alongside locals. Return to your inn for a peaceful night’s rest under starlit skies.

day 2
Historical Sites and Heritage Trails
morning
:

Begin at the Charlton Center Historic District for a self-guided walking tour of antique buildings and the town green. Snap photos of the historic church steeple and the old train station turned museum. Enjoy a light brunch at a nearby bakery famous for its cinnamon rolls.

afternoon
:

Drive to the Hopedale Heritage State Park to follow interpretive trails that highlight the park’s industrial past. Visit old mill ruins and read historic markers explaining the town’s manufacturing boom. Pack bottled water and trail snacks for a leisurely afternoon hike.

evening
:

Dine at a farm-to-table restaurant that sources ingredients from local growers. Sample seasonal dishes paired with craft beers brewed in nearby towns. Conclude your evening with a sunset stroll by the Hopedale Pond Shoreline.

day 3
Bigelow Hollow State Park Hike
morning
:

Set out early for Bigelow Hollow State Park, a short drive from Charlton, to witness mist rising off tranquil lakes. Hike the Centennial Trail, weaving through old‐growth hemlock forests and along steep ridges. Pause by the water for a moment of meditation before continuing on your path.

afternoon
:

Enjoy a packed picnic lunch at one of the park’s scenic overlooks, surrounded by the vibrant colors of ferns and wildflowers. Explore the park’s hidden coves and swimming holes, perfect for a refreshing dip on a warm day. Keep an eye out for local wildlife, including white-tailed deer and songbirds.

evening
:

Head back to Charlton for dinner at a rustic inn known for hearty New England fare like clam chowder and pot roast. Warm up by the fireplace with a locally distilled liqueur or craft cider. Reflect on the natural beauty you experienced as you relax for the evening.

day 4
Lake Chaubunagungamaug Exploration
morning
:

Drive to Lake Chaubunagungamaug (also called Webster Lake) for a serene morning paddle in a rented kayak or canoe. Glide across the glassy surface as loons call in the distance and oak-fringed shores pass by. Pull over at a sandy inlet for a snack and some lake-side bird watching.

afternoon
:

Enjoy lunch at a lakeside grill known for fresh fried clams and lobster rolls. Then sign up for a guided fishing charter, where you can cast for bass and pickerel under the guidance of experienced anglers. Learn local fishing techniques and fish tales as you cruise the lake.

evening
:

Return to Charlton’s waterfront for a lakeside sunset cruise with light appetizers and live acoustic music. Feel the gentle breeze as the sun dips below the horizon, painting the sky in rosy hues. Finish the day with a casual lakeside dinner and toasted marshmallows around a fire pit.

day 5
Horseback Riding and Farm Visit
morning
:

Head to a nearby ranch for a guided horseback ride through pastoral meadows and forest trails. Learn basic riding techniques before setting off at a leisurely pace among rolling hills. Pause at a scenic overlook to take in panoramic views of the surrounding countryside.

afternoon
:

Visit a working farm pick-your-own orchard, where you can gather crisp apples, juicy berries, and seasonal squash. Take a behind-the-scenes tour of the barn to meet friendly goats, sheep, and chickens. Indulge in a farm-fresh lunch featuring homemade pies and local cheeses.

evening
:

Dine in Charlton at a historic tavern that uses farm-grown produce and meats from local ranches. Savor a gourmet burger topped with cheddar from a nearby creamery. End the evening with a stroll through lantern-lit fields under a full moon.

day 6
Arts, Crafts and Theatre Evening
morning
:

Start with a visit to local artisan studios where potters, glassblowers, and painters work in restored mill buildings. Watch demonstrations and chat with craftsmen about their creative processes. Pick up a unique handmade souvenir to take home.

afternoon
:

Enjoy lunch at a café adjacent to an art gallery showcasing regional painters and sculptors. Then spend the afternoon in a workshop session—try your hand at wheel-throwing clay or creating stained glass panels. Learn techniques you can replicate once you return home.

evening
:

Attend a live performance at a small-town theater featuring community actors or touring musicians. Savor a pre-show dinner of farm-fresh pasta or artisanal flatbread in the theater’s bistro. Let the creative energy of the performance carry you into a memorable night.

day 7
Local Wineries and Breweries Tasting
morning
:

Travel to a boutique winery for a vineyard tour, learning about grape varieties and aging processes. Savor a tasting flight of crisp whites and full-bodied reds paired with locally made cheeses. Wander through rows of vines as the morning sun warms the air.

afternoon
:

Head to a nearby microbrewery, where you can sample craft beers brewed with local hops and grains. Enjoy a brewery tour that explains the malting, brewing, and fermentation steps. Combine your flight with gourmet pub fare like artisan sausages and pretzels.

evening
:

Return to Charlton for dinner at a gastropub famed for its beer-infused sauces and house-smoked meats. Pair your meal with a local seasonal ale or cask beer on tap. Round out the evening by toasting friends beneath string lights on an outdoor patio.

day 8
Scenic Drive and Farmstand Tour
morning
:

Embark on a scenic drive through countryside backroads lined with stone walls and red barns. Stop at seasonal farmstands to sample freshly picked strawberries, peaches, or sunflowers. Chat with farmers about heirloom produce and homemade preserves.

afternoon
:

Continue to a family-owned cranberry bog for a guided tour explaining the unique process of cranberry harvesting. Watch workers rake floating berries in shallow floodwaters and learn about the bog’s ecology. Enjoy a cranberry bread pudding or fresh-pressed juice afterward.

evening
:

Savor dinner at a local bistro that highlights produce from the very farms you visited. Try a warm squash soup or roasted beet salad made with just-harvested ingredients. Finish your evening with a homemade cranberry tart and a cup of chamomile tea.

day 9
Blackstone Gorge Kayaking and Fishing
morning
:

Drive to Blackstone Gorge for a morning of paddling through limestone chasms and emerald pools. Launch your kayak near gentle rapids and drift through quiet, forested sections. Keep an eye out for mergansers and kingfishers darting along the riverbanks.

afternoon
:

Stop for a riverside picnic lunch on smooth glacial rocks warmed by the sun. Then try your luck fishing for trout in the crystal-clear pools. If you prefer, explore hidden side channels that open up to secret waterfalls.

evening
:

Return to town and dine at a river-view restaurant offering fresh-catch specials. Sample a pan-seared trout or maple-glazed salmon paired with locally grown vegetables. Conclude your day with a moonlit riverside walk, listening to the gentle rush of water.

day 10
Farewell and Reflection
morning
:

Ease into your final day with a leisurely breakfast at a local tea house serving homemade scones. Spend your last morning exploring antique shops for vintage finds to commemorate your trip. Take time to write postcards or notes about your favorite experiences.

afternoon
:

Enjoy a farewell lunch in the town green, picnicking on artisanal cheeses, charcuterie, and fresh fruit. Revisit a favorite spot for one last photo opportunity against the backdrop of historic Charlton. Pack your car with local goodies purchased from the farmers’ market.

evening
:

Treat yourself to a spa session or massage at a nearby wellness center to unwind before your journey home. Dine at a fine-dining restaurant that offers a tasting menu showcasing the region’s best flavors. Reflect on your immersive 10-day adventure as you savor a final glass of New England cider.

Discover Charlton

Read more in our Charlton 2025 Travel Guide.

Charlton Travel Guide