Zach's Last Ride
Terminal Velocity: Zach's Last Free Fall
Zach's sending it one last time — 7 days of pure adrenaline in Jackson Hole
Home Base
The Teton Lodge Estate (2 properties, split group)
Luxury Vacation Rental (2 connected homes)
Two adjacent 6-bedroom homes with shared pool, hot tub, and outdoor fire pit — HQ for the crew. One house is the main lodge with kitchen, living room, and game room; the second is the bunkhouse with bedrooms and a second kitchen. Walking distance to hiking trailheads, 10 min to nightlife. Pricing estimated based on market rates for large group rentals in Jackson Hole June.
$2,800–$3,400/night total (split 22 ways = $127–$155/person/night)/nightDay 1 — Wheels Down, Send It Begins
Arrive at Jackson Hole Airport (JAC)
Group arrives staggered throughout early afternoon. Coordinate 3 Uber XL pickups to the lodge (15 min drive). First crew arrives by 2:30 PM, last by 3:30 PM. Drop bags, settle in, pool time.
Tip: Have the treasurer collect $1,700/person cash upfront for the group Venmo — covers lodging, activities, and shared meals.
Pool & Hot Tub Time at The Lodge
Crew decompresses at the rental — pool, hot tub, and outdoor fire pit. Zach does a quick crew intro (who's who, what's the vibe). This is the icebreaker moment for the guys who don't know each other.
Tip: Stock the cooler with Modelo Especial (Zach's drink) and local craft beers. Have the welcome kit ready on the kitchen counter.
Brewery & Distillery Crawl — Jackson Hole Town Square
First activity: Roadhouse Brewing (6:00–6:45 PM) → Snake River Brewing (7:00–7:45 PM) → Jackson Hole Still Works (8:00–8:30 PM). Walking distance, casual vibe, everyone gets oriented to the town. Zach leads the charge — this is his kind of send-it energy.
Tip: Grab a map at the first brewery. The three spots are all within 2 blocks of each other on the Town Square.
Casual Dinner — Pinky G's Pizzeria (Town Square)
Late-night pizza on the Town Square. No reservation needed, first-come-first-served. New York-style slices, cheap, and the crew can split into smaller tables. Zach picks the first round of beers.
Tip: Order 15–20 slices to start, then order more. It's cheap and nobody's too hungry after the brewery crawl.
First Night Out — The Million Dollar Cowboy Bar
Iconic honky-tonk with saddle barstools and live country music. This is the vibe-setter — rowdy, fun, and 100% Jackson Hole. Zach's crew gets loose, inside jokes start forming. No cover charge, drinks are $6–$8.
Tip: Arrive before 11:30 PM to grab the saddle barstools. The live band starts at 10:00 PM and it gets packed by midnight.
Back to The Lodge
Party bus or Uber XL back to the rental. Crew hangs at the fire pit, more beers, stories. Zach's in his element — this is the first 'send it' moment of the trip.
Tip: Leave the fire pit going — it's the natural gathering spot for the whole trip.
Day 2 — Throttle Up
Breakfast at The Lodge
Cook-at-house breakfast — eggs, bacon, toast, coffee. Crew eats together, hangs out, recovers from Day 1. No rush, no schedule. This is the downtime that builds the crew.
Tip: Stock the kitchen with eggs, bacon, and fresh fruit the night before. Assign two guys to cook — it's a bonding moment.
Downtime — Pool, Hot Tub, Yard Games
2.5-hour block with zero structure. Pool time, cornhole, cards, naps. This is where the inside jokes form. Zach hangs with different crew members, one-on-one moments happen.
Tip: Set up a speaker at the pool — Killers, Kings of Leon, Foo Fighters on rotation. Zach's vibe.
ATV / Off-Road Adventure — Snake River Valley (High Country Outfitters)
Split into two groups of 11. Group A departs 9:00 AM (already done), Group B departs 11:30 AM. 4-hour guided ride through sagebrush, river crossings, and mountain trails. Zach leads Group A — this is his adrenaline sweet spot. Helmets, gear, instruction included.
Tip: Wear layers — mornings are cool, afternoons are hot. Sunscreen is critical in June at elevation.
Group B ATV Ride (Staggered Start)
While Group A is finishing up, Group B heads out for their 4-hour ride. Same route, same guides, same adrenaline. Zach checks in with Group B before they leave — 'Send it, boys.'
Tip: Coordinate with the outfitter to have both groups back by 5:30 PM for dinner prep.
Shower & Dinner Prep at The Lodge
Both ATV groups back by 5:30 PM. Crew showers, changes, and gathers in the kitchen. Tonight is the private chef night — elevated dinner at the house.
Tip: Have the private chef arrive by 5:45 PM. They'll prep appetizers while the crew gets ready.
Private Chef Dinner — The Lodge (Reservation: 3 weeks prior)
Chef prepares a 3-course meal for 22 at the lodge. Menu: smashburger sliders with green chile (Zach's favorite), grilled vegetables, and a dessert spread. Wine and beer included. This is the crew's first big meal together — round-table introductions, toasts, and bonding.
Tip: Have the chef prepare extra green chile on the side — Zach's obsessed. Ask them to make it spicy.
Second Night Out — Bar Crawl Route: The Silver Dollar Bar → The Virginian Saloon → The Mangy Moose
Three-bar crawl starting at The Silver Dollar Bar (Wort Hotel) — historic, craft cocktails, live music. Then The Virginian Saloon (pool tables, darts, locals' vibe). End at The Mangy Moose (après-ski energy, rowdy). Party bus picks up at the lodge at 9:45 PM, drops at The Silver Dollar. Crawl takes 3 hours, party bus returns at 1:00 AM.
Tip: The Silver Dollar has 2,032 silver dollars inlaid in the bar — Zach will love the detail. Start here, end rowdy at The Mangy Moose.
Party Bus Back to The Lodge
Crew is loose, music is loud, Zach's leading the chants. Fire pit awaits.
Tip: Have the party bus driver play Killers and Foo Fighters — Zach's soundtrack.
Day 3 — Terminal Velocity (The Surprise)
Breakfast & Briefing at The Lodge
Crew gathers for breakfast. Best man announces: 'Zach, you're going skydiving.' Zach's face when he realizes it's happening — this is the moment. Tandem jump over the Grand Tetons at 13,500 ft. Two groups of 11, staggered jumps.
Tip: Film Zach's reaction when you tell him. This is the core memory of the trip.
Tandem Skydiving — Grand Teton Scenic Jump (Jackson Hole Paragliding)
Group A (11 people including Zach) departs for the jump site at 10:00 AM. Tandem jump with certified instructor, 13,500 ft altitude, 60-second freefall, Teton views the whole way down. Back by 12:30 PM. Group B jumps 1:00–3:00 PM.
Tip: Zach will be shaking with adrenaline when he lands. Have a cold Modelo waiting. This is the trip's peak moment.
Group B Skydiving (Staggered Jump)
While Group A is landing and celebrating, Group B heads to the jump site. Same experience, same views, same adrenaline. Zach watches Group B jump — he's already hooked.
Tip: Coordinate with the skydiving company to have video/photos ready. Zach will want to relive this moment.
Downtime — Pool, Recovery, Decompression
Both groups back by 3:30 PM. Crew is buzzing from the jumps. Pool time, beers, and stories. Zach's on cloud nine — literally just jumped out of a plane over the Tetons. This is the natural high point of the trip.
Tip: Let the crew decompress. No structure, no schedule. This is the moment where the trip becomes legendary in their minds.
Casual Dinner — Hatch Taqueria & Tequilas
Crew heads to Hatch for tacos, tequila, and margaritas. Casual vibe, no reservation needed, everyone's still riding the skydiving high. Zach picks the first round of tequila shots.
Tip: Sit outside if possible — June weather is perfect. Tequila and tacos are the perfect post-adrenaline meal.
Chill Night — The Rose (Cocktail Bar, Reservation: 2 weeks prior)
Upscale craft cocktail bar above the Town Square. Moody vibe, craft drinks, and a chance to decompress after the skydiving high. This is a lighter nightlife night — no party bus, just Ubers. Crew stays for 2–3 hours, then back to the lodge.
Tip: The Rose is small and intimate — perfect for a crew that's already bonded. Order the house cocktail and let the bartender make magic.
Back to The Lodge — Fire Pit & Stories
Crew gathers at the fire pit. Zach's still processing the skydive. Stories, laughs, and the realization that this trip is already legendary.
Tip: This is the night to let Zach soak in the moment. No forced activities — just the crew and the fire.
Day 4 — Peaks & Valleys
Breakfast at The Lodge
Cook-at-house breakfast. Crew's still buzzing from Day 3. Zach's already talking about the skydive — 'Did you see me freefall?' Yes, Zach. We all saw it.
Tip: Make a big breakfast — eggs, bacon, toast, fruit. The crew's earned it.
Downtime — Pool, Hot Tub, Yard Games
2.5-hour block with zero structure. This is the recovery day. Pool, cornhole, naps, cards. Zach hangs with different crew members. Inside jokes deepen.
Tip: This downtime is critical — it's where the trip becomes a memory. Don't skip it.
Grand Teton Hiking — Cascade Canyon Loop (Self-Guided)
Split into two groups of 11. Fast group departs 8:30 AM (already done), casual group departs 10:00 AM. 9.6-mile loop with 2,000 ft elevation gain. Waterfall views, alpine meadows, and Zach's in his element — he's a climber and mountain biker. Both groups meet back at the trailhead by 4:00 PM.
Tip: Bring plenty of water and snacks. June weather is perfect, but the sun is intense at elevation.
Shower & Dinner Prep at The Lodge
Hiking groups back by 4:30 PM. Crew showers and gathers. Tonight is a casual dinner — no reservations needed, no stress.
Tip: Have cold Modelos waiting when the hikers get back. They've earned it.
Casual Dinner — Trio American Bistro
Upscale bistro with a great bar and locals' vibe. No reservation needed for a group this size if you arrive by 7:00 PM (call ahead to confirm). New American cuisine, good wine list, and a relaxed atmosphere. Zach picks the appetizers.
Tip: Sit at the bar if possible — the bartender will take care of the crew. Order the house cocktails and let them flow.
Chill Night — Roadhouse Brewing Taproom
Low-key brewery night. Crew hangs at Roadhouse Brewing, plays cornhole, and drinks local craft beer. No party bus, just Ubers. This is a recovery night — no clubs, no chaos. Zach's still processing the skydive, and the crew's bonding naturally.
Tip: The Roadhouse has a great outdoor space — perfect for a chill June evening. Zach will appreciate the laid-back vibe.
Back to The Lodge — Early Night
Crew heads back by 11:00 PM. This is an early night — the trip's been intense, and everyone needs rest before the final days.
Tip: Encourage the crew to get 8 hours of sleep. The final days are big.
Day 5 — Paintball & Poker (The Roast)
Breakfast at The Lodge
Cook-at-house breakfast. Crew's rested and ready for the final push. Zach's still riding the skydive high, but today is about competition and crew bonding.
Tip: Make a big breakfast — the crew needs fuel for paintball.
Downtime — Pool, Hot Tub, Yard Games
2.5-hour block with zero structure. Pool, cornhole, naps. Zach hangs with the crew. This is the last true downtime before the final push.
Tip: Use this time to prep for the poker roast tonight. Best man should finalize his roast structure.
Paintball Battle Royale — Jackson Hole Paintball Park
Full-day paintball tournament with 22 players split into two teams. Woodsball and speedball fields, all-day rental, paint, and CO2 included. Zach leads one team — this is his kind of competitive chaos. Tournament-style play, scorekeeping, and bragging rights. Back by 4:30 PM.
Tip: Zach's competitive — he'll want to win. Make sure the teams are balanced. The losing team buys the first round of beers at the poker night.
Shower & Dinner Prep at The Lodge
Paintball crew back by 4:30 PM. Everyone showers and gathers in the kitchen. Tonight is the poker roast — the core honoring moment of the trip.
Tip: Have the kitchen stocked with snacks, beer, and whiskey. This is a long night.
Casual Dinner — Cook-at-House (Burgers & Sides)
Crew cooks burgers at the lodge — grilled smashburgers with green chile (Zach's favorite), fries, and coleslaw. BYOB, casual vibe. Everyone eats together, then transitions to the poker table.
Tip: Have extra green chile on hand. Zach will want it on everything.
Private Poker Tournament — The Lodge (Living Room)
Tournament-style poker night with 22 players. $50 buy-in, chips, cards, and whiskey. Zach hosts — this is where the roast happens. 4–5 hours of cards, stories, and laughs. The roast is structured into the poker night (see honoringMoment for full details).
Tip: Set up the poker table in the main living room with good lighting. Have a speaker playing Killers, Kings of Leon, and Foo Fighters in the background.
Back to Bedrooms — Late Night
Poker night wraps by midnight. Crew's buzzing from the roast, the competition, and the stories. Zach's been honored, roasted, and celebrated. Crew heads to bed by 1:00 AM.
Tip: The roast is the emotional peak of the trip — let it breathe. Don't rush it.
Day 6 — River Rush & Final Night
Breakfast at The Lodge
Cook-at-house breakfast. Crew's recovering from the poker roast. Zach's still glowing from being honored. One more big activity, then the final night out.
Tip: Make a hearty breakfast — eggs, bacon, toast, fruit. The crew needs fuel for the rafting.
Downtime — Pool, Hot Tub, Yard Games
2.5-hour block with zero structure. Pool, cornhole, naps. This is the last downtime before the final push. Zach hangs with the crew, soaks in the moment.
Tip: Use this time to prep for the final night — the steakhouse dinner and big bar crawl.
Snake River Whitewater Rafting — Class III Rapids (Barker-Ewing Rafting)
Split into two groups of 11. Group A departs 1:00 PM, Group B departs 3:00 PM. 4-hour guided float through Class III rapids with Teton views. Zach's done kite surfing and rock climbing — whitewater rafting is the perfect adrenaline closer. Back by 5:00 PM.
Tip: Wear layers — the water is cold in June. Sunscreen is critical. The guides will provide wetsuits.
Shower & Dinner Prep at The Lodge
Both rafting groups back by 5:30 PM. Crew showers and gathers. Tonight is the final big night — steakhouse dinner and the big bar crawl.
Tip: Have cold Modelos waiting when the rafters get back. They've earned it.
Steakhouse Dinner — The Gun Barrel Steak & Game House (Reservation: 3 weeks prior)
The tradition: final night steakhouse. The Gun Barrel is peak Wyoming — elk, bison, and wild game steaks in a lodge setting. 22 people, round-table seating, wine list, and the crew's final big meal together. Zach sits at the head of the table. This is the moment to reflect on the trip.
Tip: Order the elk steak — it's the signature. Have the sommelier pair wines for the table. This is the trip's final formal moment.
Final Bar Crawl — The Million Dollar Cowboy Bar → The Mangy Moose → The Virginian Saloon
Three-bar crawl to close out the trip. Start at The Million Dollar Cowboy Bar (honky-tonk, saddle barstools, live music). Then The Mangy Moose (après-ski energy, rowdy). End at The Virginian Saloon (pool tables, darts, locals' vibe). Party bus picks up at the steakhouse at 9:15 PM, drops at The Million Dollar Cowboy. Crawl takes 3 hours, party bus returns at 1:00 AM.
Tip: This is the final night — let it rip. Zach's been honored, he's jumped out of a plane, and he's rafted Class III rapids. The crew's earned this.
Party Bus Back to The Lodge
Crew is loose, music is loud, Zach's leading the chants one last time. Fire pit awaits for the final night.
Tip: Have the party bus driver play Killers and Foo Fighters — Zach's soundtrack for the whole trip.
Day 7 — Recovery Brunch & Departure
Recovery Brunch — Café Genevieve (Reservation: 1 week prior)
Southern-inflected brunch in a historic log cabin. Pig candy is famous. 22 people, casual vibe, no rush. Bloody marys, mimosas, and the crew's final meal together. Zach picks the first round of drinks.
Tip: Book a large table or multiple tables. The restaurant can accommodate groups if you call ahead.
Downtime — Pool, Hot Tub, Yard Games
Final 2-hour block at the lodge. Pool, cornhole, naps. Crew packs, settles up Venmo, and prepares for departure. Zach hangs with the crew one last time.
Tip: Use this time to take a final group photo at the lodge. This is the memory you'll want to keep.
Departure — Airport Runs
Coordinate 3 Uber XL pickups from the lodge to Jackson Hole Airport (15 min drive). Stagger departures based on flight times. Most flights are 3:00 PM or later — nobody needs to rush.
Tip: Have the treasurer settle the final Venmo splits before departure. Everyone should know their balance.
The Bars
The Million Dollar Cowboy Bar
Honky-tonk with saddle barstools, live country music, and unhinged energy
Iconic Jackson Hole bar with saddle barstools and live country music every night. Tourist-meets-local energy, cheap drinks ($6–$8), and the vibe-setter for the trip. Zach will love the rowdy atmosphere.
The Mangy Moose
Après-ski bar with live bands and rowdy energy
Legendary après-ski bar at Teton Village with live bands and rowdy energy. Great for the final night crawl — high energy, packed, and the perfect place to close out the trip.
The Silver Dollar Bar (Wort Hotel)
Historic bar with 2,032 silver dollars inlaid in the bar, craft cocktails, and live music
Historic 1941 bar inlaid with 2,032 silver dollars. Craft cocktails, live music, and a sophisticated vibe. Perfect for the Day 2 bar crawl — start here, end rowdy at The Mangy Moose.
The Virginian Saloon
No-frills dive bar with pool tables, darts, and a jukebox
Cash-only dive bar with pool tables, darts, and a jukebox. Locals' hangout, cheap drinks, and the perfect place to end the final night crawl. Zach will appreciate the gritty vibe.
The Rose
Upscale craft cocktail bar above Town Square with moody, intimate vibe
Craft cocktail bar above the Town Square with a moody, intimate atmosphere. Perfect for a lighter nightlife night on Day 3 — the crew can decompress after the skydiving high.
Where to Eat
The Gun Barrel Steak & Game House
Steakhouse / Game • $65–$95/person
Iconic Wyoming steakhouse with elk, bison, and wild game in a lodge setting. The final night tradition — round-table seating, wine list, and peak bachelor party energy. Zach sits at the head of the table.
Private Chef Dinner — The Lodge (Day 2)
Private Chef / Elevated Casual • $55–$75/person
3-course meal at the rental house. Menu: smashburger sliders with green chile (Zach's favorite), grilled vegetables, and dessert. Wine and beer included. Round-table bonding moment.
Hatch Taqueria & Tequilas
Mexican / Casual • $20–$35/person
Tacos, tequila, and margaritas in a lively space near Town Square. Casual vibe, no reservation needed. Perfect post-adrenaline meal after skydiving.
Trio American Bistro
New American / Upscale Casual • $40–$60/person
Upscale bistro with a great bar and locals' vibe. New American cuisine, good wine list, and a relaxed atmosphere. No reservation needed if you arrive by 7:00 PM.
Pinky G's Pizzeria
Pizza / Late-Night • $12–$20/person
New York-style slices on the Town Square. Cheap, casual, and the late-night bachelor party staple. No reservation needed, first-come-first-served.
Café Genevieve
Southern / Brunch • $25–$40/person
Southern-inflected brunch in a historic log cabin. Pig candy is famous. Bloody marys, mimosas, and the perfect recovery meal. Book a large table.
Cook-at-House Meals (Days 1, 4, 5)
Casual / DIY • $15–$25/person
Breakfast and casual dinners at the lodge. Eggs, bacon, toast, burgers with green chile. BYOB, no stress, crew bonding.
Budget Breakdown
Pack This
- - Hiking boots (for Cascade Canyon — 9.6 miles, 2,000 ft elevation gain)
- - Sunscreen SPF 50+ (June sun at elevation is intense)
- - Layers (mornings are cool, afternoons are hot; nights are cold)
- - Athletic clothes (ATV, paintball, rafting, hiking)
- - Swimsuit & towel (pool, hot tub, river)
- - Casual & nice-casual clothes (brewery crawl, steakhouse, bar crawls)
- - Closed-toe shoes (ATV, paintball, hiking)
- - Waterproof bag (for rafting — phones and wallets)
- - Headlamp or flashlight (for evening activities, fire pit)
- - Toiletries & medications (Advil, sunscreen, lip balm, deodorant)
Pro Tips
- - Zach's obsessed with 'Send It' — use it in every toast, every moment, every decision. The crew will eat it up.
- - June weather in Jackson Hole is perfect (70–80°F days, 40–50°F nights), but the sun is intense at elevation — sunscreen is non-negotiable for the ATV, hiking, and rafting.
- - Book the steakhouse (The Gun Barrel) and private chef 3+ weeks in advance for a group of 22. Same with the skydiving company — June is peak season.
- - The party bus is a game-changer — $600–$800 for the night covers transport, music, and the vibe. Worth every penny for a group this size.
- - Zach's a climber and mountain biker — the Cascade Canyon hike will blow his mind. Make sure he knows it's coming.
- - Have the skydiving video/photos ready when Zach lands. He'll want to relive it immediately.
- - The fire pit at the lodge is the natural gathering spot — keep it going all week. This is where the inside jokes form.
- - Assign a treasurer to handle the group Venmo. With 22 people, you need someone tracking lodging, activities, and shared meals.
Group Logistics
Transport: Party bus for nightlife nights (Days 2 and 6): $600–$800/night for 22 people. Uber XL for airport runs (3 pickups, 15 min each way): $40–$60/ride. Rideshare for casual nights (Days 3 and 4): $10–$20 per ride, split among 4–5 people. Total transport budget: ~$1,400–$1,800 for the week.
Nightlife Strategy: Two bar crawls (Day 2 and Day 6) with 3 bars each, plus two chill nights (Day 3 and Day 4). Day 2 crawl: The Silver Dollar Bar → The Virginian Saloon → The Mangy Moose (start sophisticated, end rowdy). Day 6 crawl: The Million Dollar Cowboy Bar → The Mangy Moose → The Virginian Saloon (reverse order, same energy). Party bus picks up at the lodge at 9:45 PM, drops at the first bar, returns at 1:00 AM. No cover charges at any venue. Drinks average $6–$10 per person per bar.