Arrive in Manhattan and stretch your legs with a walk through Bryant Park before grabbing a late-morning coffee and pastry at Culture Espresso; the park's calm lawn and city views are a great intro after the drive. Head to Chelsea Market for a casual brunch-sample oysters at The Lobster Place or tacos at Los Tacos No. 1-then stroll the High Line elevated park for river views and public art, setting you up perfectly for an afternoon of brewery hopping and neighborhood exploration.
Ease into the city afternoon with a relaxed brewery crawl in Brooklyn starting at Other Half Brewing for inventive IPAs, then stroll a few blocks to the cozy taproom at Threes Brewing to sample seasonal sours and small plates. Follow a short walk to Brooklyn Bridge Park for skyline views as golden hour approaches, then cross back toward Manhattan for an early evening flight of barrel-aged beers at The Ginger Man or a beer-paired meal near the Theater District.
As the city lights come alive, enjoy a craft-beer-forward dinner at Blind Tiger Ale House in Greenwich Village with a rotating tap list and elevated pub fare, then wander nearby to catch live jazz at Smalls Jazz Club for an intimate late-night set. If you prefer a rooftop vibe, head to 230 Fifth Rooftop Bar for skyline views and cocktails (they also list local craft beers), finishing the night with a relaxed walk through the illuminated streets of the West Village to soak in the neighborhood atmosphere.
Leave the city and enjoy a restorative drive up I-87 and scenic Route 7 into Vermont, stopping for a hearty breakfast at Marlow's Lunch in Bennington for classic diner fare and pies. Stretch your legs on the easy, fern-lined loop at Hogback Mountain Conservation Area-a 1.5-2 mile out-and-back offering colorful fall foliage views-and reward yourself afterward with a tasting flight at Fiddlehead Brewing Company in Burlington's satellite taproom (or their closest south/central VT location) to sample crisp local ales before continuing deeper into the Green Mountain countryside.
After your morning hike and a Fiddlehead tasting, head deeper into the Green Mountains with a scenic drive to Middlebury, where you can wander the historic downtown and pick up sandwiches or local cheese at Otter Creek Bakery & Deli for a picnic. Continue to Branbury State Park for an easy lakeside loop and swimming or paddling on Lake Dunmore, then finish the afternoon with a flight of farmhouse ales at Wolaver's Organic Brewery (or a nearby taproom offering Vermont saison and farmhouse styles) before settling in for dinner in town.
After settling into your Vermont base, wander the quaint streets of Woodstock Village and pop into Mon Vert Café & Bakery for a warming pastry or coffee before dinner. For a relaxed evening of local beer and live music, head to The Alchemist Taproom in Waterbury for fresh cask IPAs and a cozy beer garden, or choose Harpoon Brewery's Waterbury taproom for a flight paired with hearty Appalachian-inspired small plates.
Drive into the White Mountains and kick off the day with a sunrise walk on the easy ridge trail at Mount Willard Trail for sweeping valley and mountain vistas-perfect for fall color and stretching legs after the Vermont drive. After the hike, refuel in nearby Littleton with a hearty brunch at The Common Man (known for local ingredients) and then sample sessionable ales at Polly's Pancake Parlor & Brewery's local partner taproom or the cozy tasting room at Moat Mountain Smokehouse & Brewing Co. before heading deeper into the range for afternoon climbs.
Spend the afternoon tackling a classic White Mountains hike on the moderate Arethusa Falls Trail, following shaded forest paths to one of New England's tallest waterfalls-pack a picnic to enjoy on the rocks near the cascade. Afterward, drive toward North Conway and unwind with a tasting flight and mountain views at Tuckerman Brewing Company (or their nearby taproom) before strolling the charming shops of Settlers Green as the light softens.
As twilight falls, head into North Conway for a relaxed dinner and local brews at Moat Mountain Smokehouse & Brewing Co.-try a pint of their amber and pair it with live bluegrass if scheduled. After dinner, take a short drive to Cranmore Mountain Resort for an evening scenic chairlift (check seasonal availability) or stroll the lantern-lit lanes of Historic North Conway Village to pop into a cozy pub like The Red Parka Steakhouse & Pub for a nightcap while soaking in mountain-starred skies.
Leave the White Mountains behind for a scenic coastal drive and start with a seafood-forward breakfast at The Front Room in Portsmouth before wandering the historic waterfront and Prescott Park gardens. Stretch your legs on the dramatic headland trails at Odiorne Point State Park, then head south to Kittery for a mid-morning tasting at Smiling Hill Farm Brewery (or the nearby Kittery Trading Post Brewery pop-up), sampling crisp session ales while taking in harbor views and planning the afternoon ferry or cliffside walks along the Maine coast.
Drive south into Maine and explore the rocky coastline around Ogunquit with a stroll along the scenic Marginal Way cliff walk, pausing for photos at outlooks and a late-lunch of lobster roll at Barnacle Billy's. Continue to nearby Wells for a mellow afternoon paddle or short beach walk at Wells Beach, then unwind with coastal saisons and ocean views at Shipyard Brewing's Portland-area tasting room or a pint at the cozy, family-run Kennebunkport Brewing Company before settling into an evening in the Kennebunks.
As the sun dips, wander the lantern-lit streets of Old Orchard Beach for a lively boardwalk atmosphere, arcade fun, and seaside snacks before heading to dinner; reserve a table at The Treadwell Tavern in nearby Saco for elevated New England fare and a thoughtful local-beer list. After dinner, drive a short coastal stretch to Scarborough Marsh for a peaceful sunset stroll along the observation platforms-keep an eye out for marsh birds-and finish the night sampling small-batch saisons and barrel-aged ales at Fore River Brewing Company in Portland (their tasting flights are a great way to compare regional styles) while soaking in a relaxed, maritime pub vibe.
Depart southern Maine with a coastal-drive breakfast stop at Fort Hill Rural Life Museum in nearby York for coffee and fresh pastries before crossing into Canada; continue through New Brunswick with a scenic pull-off at Fundy National Park for a short cliffside walk to admire tidal vistas and stretch your legs. Time your arrival at Wood Islands Ferry Terminal (or opt to drive the Confederation Bridge) to catch the ferry crossing into PEI-once ashore, ease into island time with a relaxed lunch and your first pint at Hillsborough Brewing Company in Charlottetown before checking into your accommodation and exploring the waterfront.
After arriving on the island and checking in, take a gentle coastal drive to explore Victoria-by-the-Sea, wandering its arty main street, sampling local oyster plates at The Fullerton Station Eatery and browsing craft shops before a waterfront stroll. Follow with a late-afternoon visit to Basin Head Provincial Park to walk the famous singing sands and dip your toes, then cap the afternoon with a tasting flight at Gahan House Brewpub in Souris for easy-drinking island ales and a view of harbor activity as evening approaches.
As dusk falls, take a leisurely dinner on the waterfront at The Pilot House in Charlottetown for fresh PEI mussels and a crisp island lager while watching harbor lights. Afterward, stroll the nearby Victoria Row for live street music and local craft stalls, then cap the night with a relaxed pint and conversation at Red Shores Racetrack & Casino's adjacent bar-great for sampling island-brewed seasonal ales in a lively, post-travel atmosphere.
Start with a sunrise stroll and birdwatching at Peake's Wharf Boardwalk in Charlottetown, then drive south to explore the dramatic red sandstone cliffs and tidal pools at Point Prim Lighthouse-climb the tower for sweeping Gulf of St. Lawrence views. After working up an appetite, head to Upstreet Craft Brewing in downtown Charlottetown for a beer-and-breakfast style plate (try a house-made pastry or smoked fish) and a flight of small-batch pale ales before setting out for the day's coastal hikes.
Head west along the south shore to explore the windswept bluffs and tide pools at Brackley Beach National Park, then rent a kayak from PEI Kayaking Adventures for a peaceful paddle around nearby inlets and seal-spotting at low tide. Follow with a late-afternoon stop at Upstreet Brewing's Beachside Taproom (a separate pour-focused location from the downtown spot) for a flight of saison and kettle-soured ales while watching the shoreline light shift toward evening.
As the sun softens, drive west to enjoy a seafood-forward dinner at The Table Culinary Studio & Restaurant in Summerside, where island scallops and local ales pair beautifully; afterwards stroll the illuminated boardwalk at Summerside Harbourfront Theatre for harbor views and occasional live performances. Cap the night with a tasting flight at Gahan Brewing Company's Souris Taproom or the cozy, wood-paneled Island Hill Farm Brewery (check seasonal hours) to sample small-batch barrel-aged beers and chat with locals before returning to Charlottetown.
Rise early for a salt-scented hike along the bluff-top trails at Greenwich Dunes Trail in Prince Edward Island National Park, where boardwalks thread through dunes and offer dramatic views of the Northumberland Strait and migrating shorebirds. After the hike, drive to St. Peters Bay for a waterfront brunch of fresh oysters at The Table Culinary Studio & Café (St. Peters) and then pedal a short stretch of the Confederation Trail eastward, stopping at Souris Brewing Co.'s satellite taproom for a crisp pale ale to toast the morning's coastal scenery.
Spend a leisurely afternoon driving the scenic coastal loop to Panmure Island Provincial Park for a warm-sand walk and a visit to the charming Panmure Island Lighthouse, then continue to Stanley Bridge to photo the iconic arched causeway and browse local artisan shops. Finish with a late-afternoon seafood feast of steamers and lobster at Blue Mussel Café in North Rustico, paired with a tasting flight at Rustico Farm & Brewery (or their nearby taproom) while watching fishing boats come and go.
As daylight softens, take a scenic drive toward the fishing village of Souris and dine waterfront at The Dunes Studio Gallery & Café, savoring a plate of PEI scallops while watching the harbor activity. After dinner, catch sunset views from the breakwater at Souris Harbour and finish the night with a relaxed tasting flight at Gahan Brewing Company's Souris Taproom, where island saisons and experimental small-batch brews pair perfectly with live local music or a quiet harbor-side stroll.
Begin with a farm-to-table breakfast at The Red Shores Farmers' Market (Cavendish seasonal stall) sampling local cheeses and freshly baked brown bread, then take a guided tour of Green Gables Heritage Place to stroll the homestead, Lover's Lane and the evocative gardens that inspired Anne of Green Gables. Afterward, pedal a short stretch of the Confederation Trail toward Dalvay-by-the-Sea Provincial Park for a gentle shoreline walk and birdwatching before warming up with a mid-morning beer flight at Upstreet Brewing's Cavendish pop-up (check seasonal hours) to toast your final island morning.
Spend a relaxed afternoon touring local heritage and food producers beginning with a tasting menu and cidery tour at Rossignol Estate Winery & Distillery to sample island ciders and spirits paired with artisanal cheeses, then drive to Bannockburn Heritage Farm for a guided walk among heirloom crops and a chance to meet the farm animals. Finish with a scenic coastal stop at Greenwich Beach Lookoff for photo-ready dunes and an early-evening tasting of small-batch saisons at Founders' Brewpub (Cavendish) while watching the light soften over the Northumberland Strait.
Wind down your final island day with a sunset drive to North Rustico Harbour for a waterfront dinner of pan-seared scallops at The North Rustico Lobster Suppers (book ahead) while watching fishing boats slip home. After dinner, head to Cavendish Corner Shop & Taproom for a relaxed tasting flight of local saisons and a conversation with the brewer, then finish the night with a starlit walk along Brackley Beach or a cozy live-music set at The Gahan House (Cavendish branch) if scheduled.
Depart PEI early and cross the Confederation Bridge, then stop in Shediac, NB for a fresh lobster breakfast at Maisons de Pêcheur and a quick stroll along Parlee Beach Provincial Park to stretch your legs. Continue west into Quebec and detour to Rivière-du-Loup for coffee and a riverside walk at Promenade du Bas-Saint-Laurent, followed by a tasting at Microbrasserie Le Bien, Le Malt to sample regional pale ales before you settle into the long haul across Quebec toward Ontario.
Cross into Quebec and take the scenic Route 132 west to explore the riverfront village of Kamouraska, where you can stroll the cliffside belvedere and enjoy a late-lunch of smoked trout at Auberge La Grand' Maison before continuing. Later, stop in Saint-Pascal for a tasting at Microbrasserie Le Bien, Le Malt's regional counterpart (or another local microbrewery such as Le Corsaire Microbrasserie in nearby Rimouski) to sample Quebec farmhouse ales and amber lagers while soaking in Loire-like riverside panoramas as you head toward the overnight stretch westward.
After a long day of riverfront villages and microbreweries, slow the pace with a sunset visit to Montmagny Old Town Waterfront for a riverside walk and photo-friendly views of the St. Lawrence under golden light, then dine on hearty Quebecois comfort food at Bistro du Village where local charcuterie and poutine pair well with regional brews. Finish the night with a relaxed tasting flight at Noctem Artisans Brasseurs (or a nearby Laval/Québec City taproom depending on your westward progress) to sample barrel-aged stouts and saison finishes before settling into your overnight stop and preparing for the drive toward Ontario tomorrow.