PINEHURST, NORTH CAROLINA · EST. 1895

The Boys Are Going
to Pinehurst

7 courses · 4 days · 1 legendary trip — October 21–25, 2026

40ANOOP'S BDAY
—Days
—Hours
—Mins
—Secs

Who's Coming

8 players · 2 tee times
CPT
Anoop "Shooter"Birthday boy · San Diego
02
Dan "Knicks Nation"Heavy hitter · 160-yard 8 iron · in search of more rings · NYC & San Diego
03
Butch "No Bammer"Lefty — wrong-handed menace · 90+ rounds last year · San Mateo
04
Deven "Dre Country"Nashville through and through · Spring Hill, TN
05
Mini "Gilmore"Has successfully hammered a Happy Gilmore drive · Austin, TX
06
Jaewon "The Hook"Loves hooks — on the boat and off the tee · weapons cache if we need backup · Boise, ID
07
Darshan "Captain Chapman"Chapman or nothing · watch your heads · Bay Area
08
Jason "Main Street" A finer-things-in-life guy · top-shelf pours & Dodger blue · OC

The Plan

Wed → Sun · full scorecard

TWO TEE TIMES PER SLOT · SPLIT INTO TWO GROUPS OF FOUR

DateTimeWhat's Happening
WED 10/21by 6:00 PM Wheels down at RDUEveryone In By 6 Shared van ~6:30 (all bags fit) · ~1.5 hrs to the resort · check in ~8:00
~8:30 PM Dinner — The TavernHolly InnProposed Easy landing after a travel day — casual plates around the Holly Inn's antique Scottish bar
THU 10/226:45 AM Breakfast & Warmup40-Min Cushion Southern buffet, then range balls & putts — at the course by 7:25 for the 8:08
8:08 / 8:16⏱ 3.5 hrs → ~11:38 / 11:46 Pinehurst No. 32-Man Scramble Short course, 5,200 yds — warmup round, shake off the flight
12:50 / 1:00⏱ 5 hrs → ~5:50 / 6:00 PM Pinehurst No. 8Serious RoundShared Caddie Tom Fazio design · among the most scenic at Pinehurst
7:30 PM Dinner — Carolina Dining RoomCarolina HotelProposed Southern gourmet under the grand hotel's chandeliers · first scorecards get litigated
FRI 10/238:00 AM Breakfast & Warmup40-Min Cushion Buffet, then range by 8:50 — nobody steps on No. 2 cold
9:30 / 9:40⏱ 5 hrs → ~2:30 / 2:40 PM Pinehurst No. 2Serious RoundCart Path Only #3 public course in the US · more USGA championships than anywhere in America · 2024 US Open
3:50 / 4:00⏱ 2 hrs → ~5:50 / 6:00 PM The CradleWalking · Par 3Shoes Off — MandatoryT-Shirt Casual3–4 Clubs Max Longest hole is 127 yds — leave the ego at the villa. T-shirts, shorts, whatever — this is the casual round. Small bags provided: bring wedges, a putter, and one club you actually trust. Shoes come OFF — no exceptions, no excuses. And everybody orders a Transfusion — the Cradle's signature drink (vodka, grape juice, ginger ale). Loser of the round buys.
~6:00 PM Thistle Dhu18-Hole Putting CourseFree The famous putting course right by the Cradle — first-come, no tee time, putter only. Golden-hour warmdown before dinner, and secretly the best No. 2 green practice on property. Putt for who buys the first round.
7:30 PM Dinner — Pinehurst Brewing CoT-Shirt FriendlyProposed Roll straight from Thistle Dhu in whatever you're wearing — BBQ & house beers in the historic steam plant. No dress code, no changing, Transfusion buzz intact.
SAT 10/248:00 AM Breakfast & Warmup40-Min Cushion Buffet, then loosen up by 8:55 — big walking day ahead
9:36 / 9:48⏱ 5 hrs → ~2:36 / 2:48 PM Pinehurst No. 10Serious RoundWalking · Shared Caddie #20 public course in the US · biggest mover in the 2025 rankings (↑60)
3:04 / 3:12 Pinehurst No. 5Optional / TBC Victory lap for whoever's still standing — call it on the day
7:30 PM Dinner in the VillaGames Night 🃏Last Full Night In-villa dinner for the final night — cards, trash talk, and settling the week's bets. Nobody has to put on real shoes.
SUN 10/258:15 AM Breakfast · Pack · Check Out40-Min Cushion Buffet, bags packed and out — bell stand or straight into the van — then warmup by 9:30 for the closer
10:10 / 10:20⏱ 5 hrs → ~3:10 / 3:20 PM Pinehurst No. 4Serious RoundCart Path · Shared Caddie #28 public course in the US · Gil Hanse renovation · the closer
4:00 PM Van to RDUFlights 7 PM+ Arrive ~5:30 · change at the airport if needed · book Sunday departures 7:00 PM or later (or fly Monday). Earlier departures: shared ride out — TBC soon.

Serious Round = 10, 2, 8, 4 — scores count. Chips = format & logistics notes. Pace plan: ~3.5 hrs on No. 3 · ~5 hrs on 2, 8, 10 & 4 · ~2 hrs at the Cradle. Walking total: ~22–24 miles. Break in your shoes now.

The Damage

Per person · confirmed
Premier Golf Package (Wednesday night taken care of ✓)$3,820.00
Tax*$348.91
Resort fee$447.00
Shared caddie budget (No. 4, 8 & 10)~ $200.00
Drinks, merch & misc allowance~ $500.00
Balance per person~ $5,000

What's included

4 nights in a Carolina Villa (Wednesday night's covered) · three-course dinner nightly — good at any resort restaurant · Southern buffet breakfast daily · carts & practice facilities · all golf: No. 2, 4, 8, 10 & The Cradle.

The ~$500 allowance covers on-course & 19th-hole drinks, pro-shop merch, and misc. No cash on property — cards only.

All-in: ~$5,000

*Tax subject to change per local & state laws. Your $300 deposit is already credited in the number above. Resort balance is due at checkout; caddie tips & drinks settle as you go.

Logistics

Read before booking

✈ Flights In

Fly into RDU (Raleigh-Durham). Land by 6:00 PM Wednesday 10/21 — van leaves ~6:30.

Target 4:00–5:30 PM landings for a buffer.

✈ Flights Out

Sunday: van leaves the resort at 4:00 PM, RDU by ~5:30.

Book departures 7:00 PM or later — or fly Monday and nobody rushes.

⛳ Clubs & Bags

Clubs will be on property — tee off straight from the villa Thursday.

Carry bags must be under 24 lbs on No. 2, 4 & 10. Pack light.

🚐 Getting Around

Free resort shuttle to everything — call (910) 235-8403 or ext. 58403.

Sunday morning: pack + check out before the 10:10 round.

The Film Room

Required viewing

Course Study

Know the battlefield before you get there.

Course Study

More homework — watch on the plane.

Course Study

The more you watch, the fewer excuses in October.

Course Study

Steal a line or two for the serious rounds.

Course Study

Extra credit for the leaderboard hopefuls.

▶ Pinehurst on TikTok

From the resort's own account — 60 seconds of why this trip is happening.

What to Practice

You have until October

① The Turtleback Greens

No. 2's crowned greens shrug balls off the edges all day. Practice putting and chipping from off the green — the bump-and-run and the putter-from-20-yards-off are your best friends. High flop shots will betray you.

② Lag Putting

Fast, sloped surfaces everywhere. Spend range sessions on 30–50 foot lag putts — the guy who three-putts least wins the serious rounds. Speed over line.

③ Sandy Waste Areas

Miss a fairway and you're in hardpan sand and wiregrass, not rough. Practice picking the ball clean off tight/sandy lies — and accept that punching out sideways is a real strategy.

④ Wedge Distances

Domed greens mean small effective targets. Dial in your carry numbers from 60–120 yards — knowing your exact wedge yardages matters more here than 10 extra yards off the tee (sorry, Dan).

⑤ Walking Legs

~22–24 miles across the week, with No. 10 the longest hike. No training plan needed — just break in your shoes before October and maybe don't take the cart every single round between now and then.

⑥ Par-3 Sharpness

Between No. 3, the Cradle, and the short holes on the big courses, you'll hit a lot of scoring-iron tee shots. Groove your 7-iron-and-down — that's where the trip's bragging rights live.