The Long Weekend That Stays In
Rain in the forecast, temps in the fifties. Here's the case for staying anyway — and how to make three days in Wilmington and southern Vermont feel like a gift rather than a consolation prize.
- The forecast has rain and temperatures in the low 50s through the weekend. This is fine. This is actually good.
- Start every morning at Starfire Bakery on RT-9 — they roast their own coffee on site, and the maple latte (hot or iced) has become the kind of thing people in New England plan around. The iced version comes in a glass jar you keep.
- Southern Vermont's indoor and rain-friendly inventory is underrated: a 200-year-old church turned gallery, a new pottery studio, live music, covered bridges, and a craft cocktail bar that takes its charcuterie seriously.
- Memorial Day in the valley means the summer crowds haven't arrived yet. Restaurants have tables. Trails are quiet. The region is yours.
- This guide is organized loosely by time of day rather than by destination — build it in whatever order suits you.
There is a version of this long weekend that gets defeated by the weather report. You refreshed it Thursday night, saw the rain icon stacked three days deep, and started mentally rerouting — maybe the Cape, maybe just staying home. Let me offer a different read: a cool, overcast Memorial Day weekend in southern Vermont is one of the better-kept secrets in New England travel, and the people who know it tend to repeat it.
Wilmington in late May at 52 degrees with a gray sky overhead is not the same town it becomes in July. The Route 100 corridor doesn't have a traffic problem. The restaurants aren't operating on a 45-minute wait. The trails up toward Haystack or along the Deerfield River have a quality of stillness that disappears entirely once school lets out. And there is something about Vermont in the cold shoulder seasons — that specific combination of woodsmoke, wet pine, and a good bakery pulling something out of the oven — that is essentially impossible to replicate anywhere else.
Start Here, Every Morning
Before anything else, before you decide what the day is, go to Starfire Bakery. It sits on RT-9 at the edge of Wilmington — a modest storefront that has built a reputation wildly disproportionate to its size. It opens at 8 a.m. Wednesday through Monday, which gives you no excuse. The bakery's standing in the region travels well ahead of it: visitors from Boston and New York mention it in the same breath as their favorite spots in either city, and the comparisons aren't exaggerated.
Order something you wouldn't normally order. The Persian Love Cake is the obvious move, but if it's your first visit the maple latte — iced, in the jar — is the thing to start with. The jar is yours to keep, which is either a charming souvenir or your coffee cup for the rest of the weekend depending on how you look at it. The breads travel well; pick up a loaf for the rental and the afternoon takes care of itself.
The Case for Rain in the Mountains
Here is the thing about southern Vermont in the rain: the mountains absorb it differently than a coastline does. The green goes deeper. The rivers go louder. The covered bridges — and there are good ones within easy reach of Wilmington — become something you actually stop to look at rather than drive past. The Harriman Reservoir gets a particular quality of light under low clouds that makes it look like the kind of place someone would write a novel in.
The valley draws visitors from Boston and New York all summer long. Memorial Day weekend in the rain is when it belongs to everyone else.
The hiking calculus changes, but it doesn't disappear. The Molly Stark Trail along Route 9 between Brattleboro and Bennington is one of the most scenic drives in the state on any day; in a light rain it is actively cinematic. The trail to the summit of Haystack Mountain is manageable in waterproof boots, and the ridge looks directly down on the Deerfield Valley on a clear moment. You don't need to be summit-bagging to get something out of it.
Two Places to Spend an Hour You Didn't Plan On
Wilmington has quietly built a surprisingly strong arts and craft culture for a town its size, and two places in particular are worth knowing about if you find yourself with a rainy afternoon and no specific plan.
Arthouse, at 12 South Main Street in a 200-year-old Greek Revival church that used to be the Bissell Parish House, is the more established of the two. Since opening in early 2024 it has become the valley's de facto gallery for local artists — over 50 of them represented, ranging from fine art to ceramics to woodworking — with a wine and beer bar inside, charcuterie boards, original stained glass still in the windows, and a live event calendar that tends to have something on weekend evenings. It is genuinely a good place to be on a rainy Saturday afternoon, and the bar situation means you don't need to feel rushed.
The Uncommon Robin opened more recently, on Route 100 just outside downtown, and operates on a different register — quieter, more focused, studio energy rather than gallery energy. Owner Erin Robinson is a former massage therapist who found pottery during the pandemic and has turned it into the real thing: handmade mugs, bowls, tumblers, and more, all made right here in Vermont, alongside wheel and slab building classes and paint-and-sip sessions where you can customize a piece. If you have kids, or if you've ever wanted to try pottery and never had the excuse, this is an unusually low-pressure place to do it. If you just want to browse, that works too.
Saturday: A Full Slow Day
The weekend's heaviest rain tends to land on Saturday, which makes it the day to build around indoor rhythm rather than fight it.
Where to Eat and Drink
The Deerfield Valley's restaurant scene is better than it looks from the outside. Trail 87 in West Dover is the standout right now — owned and operated by chef Tyler Haydon, who came up through serious Chicago kitchens, it runs a genuinely seasonal farm-to-table menu in a room that manages to feel both polished and relaxed. The French Onion Burger on a challah bun with gruyere is the thing people quote when they recommend it. The café component runs coffee and pastries in the morning if Starfire has put you in the mood for a second stop.
For an evening that takes its craft seriously, Ten Tables by Bar and Bottle on Route 100 in West Dover is the answer. What was Deerfield Bar & Bottle has evolved into something fuller — a Vermont-inspired farm-to-table restaurant running local ingredients through a Mediterranean lens, with the same commitment to hand-squeezed cocktails, house-made syrups, and local spirits that built the bar's original reputation. It's 18-and-over, the room is small, and it fills up — both of which work in its favor.
Snow Republic Brewery, also on Route 100 in West Dover, runs the other direction — veteran-owned, West Coast vibes improbably transplanted to the Green Mountains, live music on weekends, and a rotation of craft beers that gives you something to work through on a long afternoon. Open noon to 8 p.m. every day, which is useful.
Monday: The Clear One
Memorial Day itself often cooperates. A weekend that starts with rain and fifties has a way of burning off by the long weekend's final morning — and if it does, southern Vermont reveals itself entirely differently at that point. The trails that were wet on Saturday are fragrant. The rivers are running full. The light on the Harriman Reservoir is direct and clear.
The ritual is simple: one last Starfire run before the drive home. They're open Mondays, 8 to 4. Get there early enough to have the choice of the full case. Bring something home — the bread travels well, the pastries travel extremely well, and the Persian Love Cake, in the right conditions, has been known to not make it past the Massachusetts border.
The thing about Vermont is that it doesn't perform for you. You come to it on its terms. A cold weekend in the rain is one of its actual terms, and it's a good one.
What to Pack for This Specific Weekend
If you're coming from Boston, New York, or anywhere south of Greenfield: bring layers you didn't think you'd need yet. The valley sits at around 1,500 feet — it runs 8 to 10 degrees cooler than the Hudson Valley on a spring evening, and even with daytime highs nudging the low 60s, a rainy Saturday night near the river can feel genuinely cold in a way that late May doesn't usually prepare you for. A waterproof shell. Hiking boots or trail runners with some grip. A sweater you don't mind if it smells like a fireplace for the rest of the weekend.
The rest takes care of itself. This is a valley that has been receiving visitors from the northeast corridor for the better part of a century — it knows what you need and generally has it within a 10-minute drive of wherever you're staying. And if you're bringing your dog, Tails on Trails Pet Resort just opened at 123 West Main Street in Wilmington — owner Danielle Buda runs climate-controlled suites and supervised daycare seven days a week, so you're not stuck choosing between a great dinner and your dog staring at the ceiling of a hotel room. On a rainy long weekend, when the region is quiet and the bakeries are warm and the mountains are doing their slow dramatic thing with the clouds, it is one of the better places to be in New England.
brbVT will have a full summer calendar up in the coming weeks — events, markets, and things worth driving up for through July and August. Subscribe to the brbVT Weekly to get it before anyone else.