Berkshires Golf Trip Planning Guide
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.
4 courses · 5 restaurants · 3 bars · 6 activities
Quick Facts
Summer, Fall
ALB (50 min drive)
$40–$140
$500/night
3 of 4
~$388/person
Sample 3-Day Itinerary
Here's a realistic 3-day itinerary for a group golf trip to Berkshires. Every venue below is real and pulled from our curated database — no filler.
Day 1
Taconic Golf Club — mountain, $85–$140 · 4.5★
Wayne Stiles classic set against Mount Greylock — one of the best public courses in New England
Nudel — farm to-table, $$$
Lenox gem with a rotating farm-to-table menu — tiny space, huge flavors, excellent wine list
The Well — cocktail · Open late
Great Barrington cocktail bar with craft drinks, small plates, and a moody vibe
Day 2
Cranwell Resort Golf Course — resort, $75–$125 · 4.3★
Stiles & Van Kleek design on the grounds of a former Gilded Age estate — now part of Miraval Resort
Jiminy Peak Mountain Adventure Park — 2-3 hours, $35–$70/pp
Alpine mountain coaster, Soaring Eagle zipline, aerial adventure park, and Eurobungy trampolines at a ski resort turned summer playground. Available for private group rental midweek. Perfect arrival-day competition.
The Old Inn on the Green — farm to-table, $$$$
Candlelit prix-fixe dinners in a 1760 stagecoach inn — unforgettable group dining experience
Brick House Pub — dive · Open late
Housatonic dive bar with live music, cheap beers, and zero pretense
Day 3
Waubeeka Golf Links — parkland, $45–$75 · 4.3★
Williamstown gem in the shadow of the Green Mountains — friendly layout with excellent fall foliage
Tanglewood Music Festival — half day, $25–$100/pp
Boston Symphony summer home — lawn seats with wine and a picnic is a quintessential Berkshires experience
Trattoria Rustica — italian, $
Pittsfield Italian with handmade pasta and a great patio — hearty portions for hungry golfers
Barrington Brewery — brewpub
Farm brewery in Great Barrington with house ales, pub food, and a big outdoor space
Course-by-Course Guide
Berkshires has 4 courses worth playing. 3 are walkable if you want to save on cart fees.
Taconic Golf Club
PremiumWayne Stiles classic set against Mount Greylock — one of the best public courses in New England
Cranwell Resort Golf Course
PremiumStiles & Van Kleek design on the grounds of a former Gilded Age estate — now part of Miraval Resort
Waubeeka Golf Links
SolidWilliamstown gem in the shadow of the Green Mountains — friendly layout with excellent fall foliage
Wahconah Country Club
SolidSemi-private course in Dalton with tree-lined fairways and a classic New England feel
Where to Stay
Berkshires has 2 group-friendly lodging options in our database, starting at $500/night for the whole house. Several options include hot tubs — a non-negotiable for most groups.
$600–$2000/night
Sleeps 10–16 · Lenox / Great Barrington area
$500–$1600/night
Sleeps 8–14 · Stockbridge / Lee area
Group Dining Guide
5 restaurants vetted for group golf trips. Several can handle large parties without a reservation headache.
Nudel
$$$Lenox gem with a rotating farm-to-table menu — tiny space, huge flavors, excellent wine list
The Old Inn on the Green
$$$$Candlelit prix-fixe dinners in a 1760 stagecoach inn — unforgettable group dining experience
Trattoria Rustica
$Pittsfield Italian with handmade pasta and a great patio — hearty portions for hungry golfers
SoCo Creamery & Cafe
$Great Barrington lunch spot with creative sandwiches and house-made ice cream
RARE 297 Steakhouse
$$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
3 bars curated for groups. 2 stay open past midnight.
The Well
Late NightGreat Barrington cocktail bar with craft drinks, small plates, and a moody vibe
Brick House Pub
Late NightHousatonic dive bar with live music, cheap beers, and zero pretense
Barrington Brewery
Farm brewery in Great Barrington with house ales, pub food, and a big outdoor space
Activities Beyond Golf
6 off-course activities for rest days or afternoons.
Jiminy Peak Mountain Adventure Park
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
Boston Symphony summer home — lawn seats with wine and a picnic is a quintessential Berkshires experience
Mount Greylock Summit Hike
Highest point in Massachusetts — drive up or hike for panoramic views of 5 states
Berkshire Brewing Company Tour
South Deerfield brewery with tours, tastings, and a loyal following for their Steel Rail pale ale
Jiminy Peak Mountain Adventure
Summer mountain coaster, zip line, and aerial park at a ski resort — group-friendly arrival day adrenaline
Berkshire Scenic Railway
Wine train experience through the Berkshire countryside — tasting room on rails
Getting There
Fly into Albany International Airport (ALB) — it's a 50-minute drive to Berkshires. For groups of 8+, consider booking a shuttle or party bus from the airport (local providers include Berkshire Limousine and Abbott's Limousine). Renting two SUVs usually works for groups of 4-8.