Berkshires Bachelor Party Golf Trip
Berkshires checks every box for a bachelor party golf trip: 4 courses for competitive rounds, 3 bars for the nights (2 open past midnight), 5 group-friendly restaurants, and 6 off-course activities when you need a break from the links.
4 courses · 2 late-night bars · 6 activities
Sample Bachelor Party Weekend
A 3-day bachelor party itinerary using real venues in Berkshires. Adjust to your crew's vibe.
Day 1 — Arrival & Night Out
Jiminy Peak Mountain Adventure Park — 2-3 hours, $35–$70/pp
RARE 297 Steakhouse — steakhouse, $$
The Well — cocktail · Open late
Day 2 — Main Event
Taconic Golf Club — $85–$140
Cranwell Resort Golf Course — $75–$125
Nudel — farm to-table, $$$
Brick House Pub — dive · Open late
Day 3 — Last Round
Waubeeka Golf Links — $45–$75
Bar Guide
2 spots stay open past midnight — critical for a proper bachelor party.
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
Group Lodging (Sleeps 8+)
$600–$2000/night
Lenox / Great Barrington area
$500–$1600/night
Stockbridge / Lee area
Best Courses for the Competition
2 premium/bucket-list courses for the main event rounds.
Transportation
$150–$225/hr · Fits 10–14
Providers: Berkshire Limousine, Abbott's Limousine · Can do golf AM + bars PM