Ease into your first morning with a relaxed coffee and pastry at Corner Roasters, then stroll the nearby Riverside Promenade to stretch your legs and get a feel for the city's rhythm. Follow the walk with a light, guided introduction to local history at the small but charming City Heritage Center, where maps and exhibits will help you plan the rest of today and orient you to neighborhood highlights.
After your leisurely morning, wander to the vibrant Old Market Square for people-watching and street musicians, then join a guided tasting at Market Lane Delicacies to sample local cheeses, charcuterie, and a seasonal craft beer or soda. Finish the afternoon with a gentle, scenic loop through Maple Park, where a short bench-side history plaque tour and a photo stop at the Sunset Gazebo set you up perfectly for an evening meal nearby.
As twilight falls, head to Harborview Terrace for panoramic river and skyline views, then settle into a relaxed dinner at the cozy Lantern Bistro, where a seasonal tasting menu paired with local wines makes for a memorable first-night meal. After dinner, take a short stroll to Moonlight Walkway, a softly lit riverside path with live acoustic performers on weekend nights, perfect for digesting and planning tomorrow's adventures.
Start your day with a lively breakfast at Sunlit Café & Bakery, savoring their signature almond croissant and a locally roasted pour-over before heading to the nearby Grand Art Museum for a concise highlights tour of contemporary and regional works. After soaking up the exhibits, take a guided walking tour through the historic Merchant Row, where period architecture, artisan shops, and a stop at Founders' Courtyard reveal the stories that connect today's city to yesterday's arrivals.
After a morning among galleries and historic streets, head to Old Harbor Wharf for a waterfront lunch at Seafarer's Eatery, where fresh seafood and harbor views set a relaxed pace; afterward join a narrated harbor cruise from Blue Wave Dock to see the city skyline and industrial heritage from the water. Finish the afternoon with a stroll through the leafy lanes of Beacon Hill Gardens, pausing at the sculpted fountains and the small seasonal craft market to pick up local artisan goods before returning toward the evening neighborhood for dinner.
As the city lights come alive, head to Skyline Roofbar for signature cocktails and a sweeping sunset view that frames the landmarks you visited earlier in the day. After drinks, enjoy an intimate dinner at Old Lantern Supper Club, where seasonal small plates spotlight local producers, then cap the night with a lively performance at the nearby Starlight Playhouse-a perfect blend of culinary comfort and local culture to round out your day.
Wake up refreshed and drive into the hills for a leisurely tasting at Shady Brook Vineyards, where a guided tasting of their estate chardonnays and crisp rosés pairs perfectly with a warm pastry from the on-site café; linger on the terrace to enjoy sweeping valley views. Continue to Laurel Creek Winery for a behind-the-scenes tour of the barrel room and a small-group vertical tasting, then stroll the property's snow-dusted walking trail to work up an appetite before a relaxed vineyard-side lunch.
Drive a short scenic route to Mountaintop Cellars for a leisurely tasting flight focused on cold-climate reds and a guided talk on local viticulture, then enjoy a cheese board on their heated porch while watching the valley light. Later, visit the family-run Fox Hollow Cidery & Taproom for a contrasting tasting of sparkling apple wines and hard ciders paired with wood-fired flatbreads, perfect for unwinding before your evening plans.
As dusk settles, drive to the cozy hilltop tasting room at Silver Ridge Winery for a candlelit tasting of their reserve port-style wine paired with local truffles while the valley lights begin to twinkle. Follow that with a short hop to Hearthside Bistro & Cellar for a rustic dinner where chef-driven small plates highlight regional game and root vegetables alongside a curated bottle from nearby producers, then end the night with a nightcap by the fireplace at The Pine Lodge Taproom, swapping tasting notes and planning a relaxed departure the next morning.