© The Red Lion Inn

Thirst for New England’s charms can be quenched by many delicious East Coast destinations that brim with Early American history, savory culinary flavors, cozy comfort accommodations and gracious good cheer. One of the region’s treasures is the storybook-like town of Stockbridge in the picturesque Berkshire Mountains of Western Massachusetts. Year-round, the beauty and bounty of the four seasons unfold here in welcoming ways, anchored by The Red Lion Inn. The festive holidays and fireplace-crackling winter ahead infuse a special seasonal joy.

LET THE MUSIC MOVE YOU

You likely have already heard about this beloved town, as in the lyrics to James Taylor’s 1970 song, Sweet Baby James: "The first of December was covered with snow, and so was the turnpike from Stockbridge to Boston." Approximately 130 miles west of Boston, a Stockbridge eatery also inspired Arlo Guthrie’s 1967 epic song, Alice’s Restaurant. (See below for music festival info.)

REST ON A PRETTY PORCH

Overlooking Stockbridge’s Main Street, the wide porch and its rocking chairs.© The Red Lion Inn

Founded in 1773, The Red Lion Inn began as a wee tavern and popular stagecoach stop, then grew through several momentous transitions. Now with an expanded historical main building plus stand-alone Village Houses and a Maple Glen contemporary-country annex, Red Lion Inn has served as a getaway for five presidents — Grover Cleveland, William McKinley, Theodore Roosevelt, Calvin Coolidge and Franklin Roosevelt — as well as for accomplished actors, artists, musicians and writers: Bob Dylan, John Wayne, Henry Wadsworth Longfellow, Nathaniel Hawthorne, Thornton Wilder and William Cullen Bryant. Today, Norman, the cat, serves as the inn’s feline ambassador — sitting, scurrying or snoozing in the large entrance room, spying the goings-on.

EAT, DRINK AND BE MERRY

Candlelight, crystal chandeliers, antique china, colonial pewter and oil paintings.© The Red Lion Inn

The inn’s three restaurants — Main Dining Room, Widow Bingham’s Tavern and Lion’s Den Pub — are especially comforting in winter, when butternut squash soup, hearty New England roasts, apple pie and a medley of fine cheeses are menu favorites. (A fourth restaurant, The Courtyard, on the terrace, is open during warm weather months.) The commitment to applaudable gourmet and casual cuisine is a priority; teamwork spirit among the staff is evident. Its ambitious wine collection is sourced worldwide, numbering more than 560 different selections. Wine Spectator has repeatedly awarded the Red Lion Inn its Best Award of Excellence. At the downstairs full-service pub, music — folk, reggae, rock, R&B by local and regional artists — is performed on a stage; no cover charge. Guests at the Main Dining Room often sip pre-dinner cocktails while listening to a pianist tinkle the ivories of a grand piano on the first floor. Since its beginning, this hotel has always been privately owned and run. Currently overseen by the Fitzpatrick family, for generations a Stockbridge mainstay, the baton is now passed to its granddaughter Sarah Eustis, who steers Red Lion Inn’s reins to the future as CEO.

SAY GOOD NIGHT

Guest rooms are designed in a multitude of shapes, sizes and styles.© The Red Lion Inn

Staying at the Red Lion Inn is a step back into slower-pace yesteryear married with modern amenities of today: complementary wifi, year-round heated outdoor pool and hot tub, air conditioning and nightly turn-down service. The Seven Salon Spa, in partnership with the inn, offers such invigorating massages as craniosacral and Thai as well as soothing body treatments such as salt scrubs and clay masks.

SHOP HAPPILY

Small boutiques: chock full of art, books, clothing, music, tea and more.© The Red Lion Inn

Among Stockbridge’s quaint and colorful shops, these are particularly popular: Peace, Love & Chocolate with bonbons, biscotti and pastries; 7 Arts Gift Shop with a diverse stock of vintage vinyl, CDs, humorous signs and knickknacks; Mutability in Motion with handcrafted jewelry, kitchenware, pottery and soaps made by USA artists and craftspeople; Williams & Sons Country Store (since the 1790s) with candles, jams, maple syrup and puzzles; and Charles H. Baldwin & Sons (since 1888), which manufactures its own pure vanilla extract, vanilla vinaigrette, vanilla-cinnamon sugar and bay rum aftershave. For a more modern outlook, feast on eye-candy at Schantz Galleries, specializing in glass sculptures; it has sold work by innovative notables, such as Dale Chihuly, Lino Tagliapietra and Bertil Vallien. 

DISCOVER AMERICAN ART

Norman Rockwell’s original Stockbridge studio.© Art Evans / Norman Rockwell Museum

Artist Norman Rockwell lived and worked in Stockbridge for the last decades of his life. The Norman Rockwell Museum, set on 63 picturesque acres, houses the largest collection of original Rockwell art in the world. Rockwell masterminded 323 eye-opening, thought-provoking, influential covers for The Saturday Evening Post, which are displayed chronologically together — an ode to his vision of America. That installation also interestingly illustrates his skilled progress as an artist.

Rockwell’s iconic, 1967 painting: Stockbridge Main Street at Christmas.© Norman Rockwell Family Agency. Norman Rockwell Museum Collections.

The Rockwell museum also spotlights temporary exhibitions of others’ work, such as the present show Frank E. Schoonover American Visions, which salutes adventure, courage, wanderlust and wilderness. Painter Schoonover tested his own mettle on gutsy, grand excursions to Alaska and Canada, which dramatically motivated his work.

GET WRAPPED UP IN HOLIDAY FUN

Christmas merriment.

Stockbridge’s Main Street at Christmas celebration (November 30, December 1 and 2) trumpets caroling, concerts, holiday readings, horse-drawn rides, house tours and vintage automobiles. Feel the magic of a tight-knit community amid twinkling lights, ornate wreaths and decorated trees.

Sleigh ride snuggling.

EXPLORE MORE SEASONS

Spring, summer and early autumn are the most active times for bird watching, cycling and hiking. For spectacular musical performances, treat yourself to tickets at Tanglewood — the warm-weather home of the Boston Pops Orchestra (in nearby Lenox). Relish, too, The Berkshire Theatre Group, toasting its 90th year, heralding shows at its Fitzpatrick Main Stage and Unicorn Theatre (in Stockbridge) and Colonial Theatre (in nearby Pittsfield). The Bidwell House Museum, a living history museum, harkens back to the 1760s (in nearby Monterey). And Chesterwood — the former home of America’s foremost 20th-century sculptor Daniel Chester French, who is most well-known for creating the Lincoln Memorial in Washington, DC — is an approximately 150-acre estate. Replete with museum, studio and sculpture garden and affiliated with the National Trust for Historic Preservation, it is enchanting.

For more travel ideas and tips: Stockbridge Chamber of Commerce and Massachusetts Vacation.

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Thirst for New England’s charms can be quenched by many delicious East Coast destinations that brim with Early American history, savory culinary flavors, cozy comfort accommodations and gracious good cheer. One of the region’s treasures is the storybook-like town of Stockbridge in the picturesque Berkshire Mountains of Western Massachusetts. Year-round, the beauty and bounty of the four seasons unfold here in welcoming ways, anchored by The Red Lion Inn. The festive holidays and fireplace-crackling winter ahead infuse a special seasonal joy.

LET THE MUSIC MOVE YOU

You likely have already heard about this beloved town, as in the lyrics to James Taylor’s 1970 song, Sweet Baby James: “The first of December was covered with snow, and so was the turnpike from Stockbridge to Boston.” Approximately 130 miles west of Boston, a Stockbridge eatery also inspired Arlo Guthrie’s 1967 epic song, Alice’s Restaurant. (See below for music festival info.)

REST ON A PRETTY PORCH

Overlooking Stockbridge’s Main Street, the wide porch and its rocking chairs.© The Red Lion Inn

Founded in 1773, The Red Lion Inn began as a wee tavern and popular stagecoach stop, then grew through several momentous transitions. Now with an expanded historical main building plus stand-alone Village Houses and a Maple Glen contemporary-country annex, Red Lion Inn has served as a getaway for five presidents — Grover Cleveland, William McKinley, Theodore Roosevelt, Calvin Coolidge and Franklin Roosevelt — as well as for accomplished actors, artists, musicians and writers: Bob Dylan, John Wayne, Henry Wadsworth Longfellow, Nathaniel Hawthorne, Thornton Wilder and William Cullen Bryant. Today, Norman, the cat, serves as the inn’s feline ambassador — sitting, scurrying or snoozing in the large entrance room, spying the goings-on.

EAT, DRINK AND BE MERRY

Candlelight, crystal chandeliers, antique china, colonial pewter and oil paintings.© The Red Lion Inn

The inn’s three restaurants — Main Dining Room, Widow Bingham’s Tavern and Lion’s Den Pub — are especially comforting in winter, when butternut squash soup, hearty New England roasts, apple pie and a medley of fine cheeses are menu favorites. (A fourth restaurant, The Courtyard, on the terrace, is open during warm weather months.) The commitment to applaudable gourmet and casual cuisine is a priority; teamwork spirit among the staff is evident. Its ambitious wine collection is sourced worldwide, numbering more than 560 different selections. Wine Spectator has repeatedly awarded the Red Lion Inn its Best Award of Excellence. At the downstairs full-service pub, music — folk, reggae, rock, R&B by local and regional artists — is performed on a stage; no cover charge. Guests at the Main Dining Room often sip pre-dinner cocktails while listening to a pianist tinkle the ivories of a grand piano on the first floor. Since its beginning, this hotel has always been privately owned and run. Currently overseen by the Fitzpatrick family, for generations a Stockbridge mainstay, the baton is now passed to its granddaughter Sarah Eustis, who steers Red Lion Inn’s reins to the future as CEO.

SAY GOOD NIGHT

Guest rooms are designed in a multitude of shapes, sizes and styles.© The Red Lion Inn

Staying at the Red Lion Inn is a step back into slower-pace yesteryear married with modern amenities of today: complementary wifi, year-round heated outdoor pool and hot tub, air conditioning and nightly turn-down service. The Seven Salon Spa, in partnership with the inn, offers such invigorating massages as craniosacral and Thai as well as soothing body treatments such as salt scrubs and clay masks.

SHOP HAPPILY

Small boutiques: chock full of art, books, clothing, music, tea and more.© The Red Lion Inn

Among Stockbridge’s quaint and colorful shops, these are particularly popular: Peace, Love & Chocolate with bonbons, biscotti and pastries; 7 Arts Gift Shop with a diverse stock of vintage vinyl, CDs, humorous signs and knickknacks; Mutability in Motion with handcrafted jewelry, kitchenware, pottery and soaps made by USA artists and craftspeople; Williams & Sons Country Store (since the 1790s) with candles, jams, maple syrup and puzzles; and Charles H. Baldwin & Sons (since 1888), which manufactures its own pure vanilla extract, vanilla vinaigrette, vanilla-cinnamon sugar and bay rum aftershave. For a more modern outlook, feast on eye-candy at Schantz Galleries, specializing in glass sculptures; it has sold work by innovative notables, such as Dale Chihuly, Lino Tagliapietra and Bertil Vallien. 

DISCOVER AMERICAN ART

Norman Rockwell’s original Stockbridge studio.© Art Evans / Norman Rockwell Museum

Artist Norman Rockwell lived and worked in Stockbridge for the last decades of his life. The Norman Rockwell Museum, set on 63 picturesque acres, houses the largest collection of original Rockwell art in the world. Rockwell masterminded 323 eye-opening, thought-provoking, influential covers for The Saturday Evening Post, which are displayed chronologically together — an ode to his vision of America. That installation also interestingly illustrates his skilled progress as an artist.

Rockwell’s iconic, 1967 painting: Stockbridge Main Street at Christmas.© Norman Rockwell Family Agency. Norman Rockwell Museum Collections.

The Rockwell museum also spotlights temporary exhibitions of others’ work, such as the present show Frank E. Schoonover American Visions, which salutes adventure, courage, wanderlust and wilderness. Painter Schoonover tested his own mettle on gutsy, grand excursions to Alaska and Canada, which dramatically motivated his work.

GET WRAPPED UP IN HOLIDAY FUN

Stockbridge’s Main Street at Christmas celebration (November 30, December 1 and 2) trumpets caroling, concerts, holiday readings, horse-drawn rides, house tours and vintage automobiles. Feel the magic of a tight-knit community amid twinkling lights, ornate wreaths and decorated trees.

EXPLORE MORE SEASONS

Spring, summer and early autumn are the most active times for bird watching, cycling and hiking. For spectacular musical performances, treat yourself to tickets at Tanglewood — the warm-weather home of the Boston Pops Orchestra (in nearby Lenox). Relish, too, The Berkshire Theatre Group, toasting its 90th year, heralding shows at its Fitzpatrick Main Stage and Unicorn Theatre (in Stockbridge) and Colonial Theatre (in nearby Pittsfield). The Bidwell House Museum, a living history museum, harkens back to the 1760s (in nearby Monterey). And Chesterwood — the former home of America’s foremost 20th-century sculptor Daniel Chester French, who is most well-known for creating the Lincoln Memorial in Washington, DC — is an approximately 150-acre estate. Replete with museum, studio and sculpture garden and affiliated with the National Trust for Historic Preservation, it is enchanting.

For more travel ideas and tips: Stockbridge Chamber of Commerce and Massachusetts Vacation.