Alright, I'll play along for the Winter Games, too. I still think that if you're the 27th most important city in the world, then it's the Summer Games you should be shooting for. But Boston hosting the Winter Games would be awesome as well--and definitely easier. Here's how I'd do it.
Ceremonies: Gillette Stadium is simply not a viable option for the Opening and Closing Ceremonies. There is absolutely no recent precedent for holding the ceremonies 30 miles away from the host city, the village, and the urban venues. Just imagine what a disaster that pitch would be:
USOC: We think Boston should host the Winter Olympics because it's a world class, globally connected city that's well situated to welcome the international community.
IOC: Great! That's just what we like to hear. Tell me, where in Boston will the opening and closing ceremonies be held? As you know, these are our two most important events.
USOC: Oh, they won't be held in Boston.
IOC: Uhhh...
USOC: They'll be held in a small town 30 miles outside of Boston.
IOC: Umm, ok, is that where everything else will be? The Olympic village, the media center, the hotels?
USOC: No. We'll just move 60,000 people en masse from Boston to Foxboro before the ceremonies, then move them all back afterwards. Then we'll do that again in two weeks.
IOC: We generally don't like to hold the Opening Ceremony in the middle of nowhere.
USOC: It's not in the middle of nowhere, there's a Bass Pro Shops right next to it!
IOC: Next!
It's not going to work. But that's fine. The stadium can be built in the same place I proposed it for the summer games. We all know that the Revs are going to end up in a soccer specific stadium in Boston sometime in the next 20 years. It's going to get built. So we kill two birds with one stone and build it for the Olympics first.
Olympic Village: same location as the summer proposal.
Olympic Flame: I loved what Vancouver did in putting the cauldron not on the edge of the stadium but in a unique place in the central city, so how about this. Ohno runs the torch into the stadium, does a lap, and hands it off to Heiden. Heiden runs it back out of the stadium and down to the Lechemere Canal where Mike Eruzione is at the helm of a duck boat carrying the 1980 Olympic hockey team! Rizzo plunges the boat into the water and takes it under the Longfellow Bridge into the Charles River Basin. The boat stops. The water begins to bubble. And just like the freaking Red October, the Olympic Cauldron surfaces and rises out of the river! Rizzo lights it, and now you have the most memorable and picturesque Olympic Flame of all time! I mean, just picture the cauldron dropped into the middle of this scene below, with chunks of ice in the river and the flame complementing the gold dome of the state house:
Phenomenal. Of course, I should mention that this is only Plan B. In Plan A, which is weather permitting, Ohno runs the flame into the stadium and hands it to the hockey team inside. As a team they run out of the stadium to the Lechemere Canal, where Eric Heiden is LACED UP and waiting for the torch on the polar vortexed canal! He takes the torch from Rizzo and skates the fucking thing out into the river! He gets to a seemingly desolate spot in the middle of the basin, raises the torch above his head, and then the ice in front of him (actually plexiglass) begins to crack! The cauldron shatters the "ice" and raises up out of the river for Heiden to light it! This would be, hands down, the greatest Olympic Flame lighting of all-time. They would just stop doing it after this one, knowing that it would never be topped.
Figure Skating: TD Garden
Hockey: Build a temporary dome over Alumni Stadium and temporary rink inside (the NHL is getting pretty good at impromptu rinks these days, it shouldn't be too hard). You've got a 20,000 seat venue for all hockey games and the ice can be built to Olympic standards.
Long Track: Clemente Field in the Fens. Why not? Eric Heiden won five gold medals skating outside in Lake Placid, let's bring it back outdoors! If the Winter Classic tells us anything, it's that people have an irrational love of doing inside things outside. Besides, how amazing would it be the watch the skaters hit the turns in front of this backdrop:
This would be the coolest Winter Olympic venue of all-time.
Short Track: TD Garden
Curling: Agganis
Cross-Country Skiing: What? Cross-country skiing as an urban event? You're damn right. Oh, and I lied when I said that speed skating in the Fens would be the coolest Winter Olympic venue of all-time, because THIS is the coolest Winter Olympic venue of all-time:
That trail is 13.8 km. Add a loop or two around the arboretum and Jamaica Pond or take the trail through the woods surrounding the VFW Parkway and you have plenty of room to host the 5, 10, 15 and 20 km races. There's plenty of room in the Blue Hills to do the 30 and 50, so all cross-country events can be held within 128. Can you imagine who cool this would be?
"Here we are at the start of the Men's 15 km in beautiful Arnold Arboretum, where the skiers are immediately challenged by the highest hills the in the city of Boston!"
"The racers have survived the hills of the arboretum, made there way down Arborway, and and now race along the shore of frozen Jamaica pond."
"Now they hit a second set of hills in Olmstead Park, the hidden jewel of the Emerald Necklace!"
"The leaders have taken control along the banks of the Muddy River!"
"Downtown Boston is in sight as they enter the Fens and glide past the long track!"
"They hit the straight-away and fly past the mansions of Commonwealth Avenue!"
"Only one turn left as they head down Boylston Street next to the Public Garden!"
"Down the stretch they come! The gold dome of the State House glitters like the gold in their dreams!"
Simply the greatest winter games of all-time...