Plan Your Berkshires Golf Trip in 60 Seconds

Refined New England golf wrapped in art, culture, and mountain scenery

The Berkshires offer a surprisingly upscale golf trip with rolling mountain courses, world-class arts venues, and a farm-to-table food scene rivaling any major city. Play courses through the Taconic Range, catch live music at Tanglewood, and dine at James Beard-recognized restaurants. A more refined trip that still delivers on the golf.

The best courses, bars, and rentals in Berkshires — curated for groups.

4 coursesSummer, FallALB (50 min drive)10-50k population

Courses

Taconic Golf Club

Premium

Wayne Stiles classic set against Mount Greylock — one of the best public courses in New England

$85-$140mountainPar 71 · 6,640 ydsWalkable

Cranwell Resort Golf Course

Premium

Stiles & Van Kleek design on the grounds of a former Gilded Age estate — now part of Miraval Resort

$75-$125resortPar 71 · 6,387 yds

Waubeeka Golf Links

Solid

Williamstown gem in the shadow of the Green Mountains — friendly layout with excellent fall foliage

$45-$75parklandPar 72 · 6,324 ydsWalkable

Wahconah Country Club

Solid

Semi-private course in Dalton with tree-lined fairways and a classic New England feel

$40-$65parklandPar 71 · 6,506 ydsWalkable

Where to Stay

houseSleeps 10-16

$600-$2000/night

Lenox / Great Barrington area

poolhot tubmountain viewsfire pitchef kitchen

houseSleeps 8-14

$500-$1600/night

Stockbridge / Lee area

lake accesskayaksfire pitmultiple bedrooms

Dining

Nudel

$$$

farm-to-table

Lenox gem with a rotating farm-to-table menu — tiny space, huge flavors, excellent wine list

The Old Inn on the Green

$$$$

farm-to-table

Candlelit prix-fixe dinners in a 1760 stagecoach inn — unforgettable group dining experience

Trattoria Rustica

italian

Pittsfield Italian with handmade pasta and a great patio — hearty portions for hungry golfers

SoCo Creamery & Cafe

casual

Great Barrington lunch spot with creative sandwiches and house-made ice cream

RARE 297 Steakhouse

steakhouse

Premium steaks, sushi, and seafood inside the historic Hotel on North in Pittsfield. Private banquet hall seats up to 234. Bar open until 1am Fri-Sat. Opened 2024 and already the go-to steakhouse in the Berkshires.

Nightlife

The Well

Late Night

cocktail

Great Barrington cocktail bar with craft drinks, small plates, and a moody vibe

Brick House Pub

Late Night

dive

Housatonic dive bar with live music, cheap beers, and zero pretense

Barrington Brewery

brewpub

Farm brewery in Great Barrington with house ales, pub food, and a big outdoor space

Activities

Jiminy Peak Mountain Adventure Park

zipline2-3 hours$35-$70/pp

Alpine mountain coaster, Soaring Eagle zipline, aerial adventure park, and Eurobungy trampolines at a ski resort turned summer playground. Available for private group rental midweek. Perfect arrival-day competition.

Tanglewood Music Festival

breweryhalf day$25-$100/pp

Boston Symphony summer home — lawn seats with wine and a picnic is a quintessential Berkshires experience

Mount Greylock Summit Hike

hikinghalf day$10-$20/pp

Highest point in Massachusetts — drive up or hike for panoramic views of 5 states

Berkshire Brewing Company Tour

brewery2-3 hours$10-$25/pp

South Deerfield brewery with tours, tastings, and a loyal following for their Steel Rail pale ale

Jiminy Peak Mountain Adventure

zipline2-3 hours$35-$70/pp

Summer mountain coaster, zip line, and aerial park at a ski resort — group-friendly arrival day adrenaline

Berkshire Scenic Railway

winery2-3 hours$20-$45/pp

Wine train experience through the Berkshire countryside — tasting room on rails

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