Hillside

Day Trips

Make the most of your day with our curated plans, packed with Hillside's hidden gems and unique experiences!

day 1
Sunrise Ridge Exploration
morning
:

Wake up before dawn and ascend the winding Sunrise Ridge Trail to catch a kaleidoscope of color as the sun peeks over the horizon. The crisp mountain air carries the scent of pine and wildflowers, setting a tranquil tone for the day. Pause at a rocky overlook to enjoy a cup of locally roasted coffee while listening to distant bird calls.

afternoon
:

Continue deeper into the ridgeline, where a knowledgeable guide will point out native plants and unique rock formations shaped by centuries of erosion. Hike past a field of vibrant lupine and learn about native medicinal herbs the local tribes once used. Stop at a shaded glade for a light picnic of fresh bread, cheese, and seasonal fruit.

evening
:

Head back down just in time for a sunset view that bathes the valley in warm, golden light. Gather around a campfire at the base of the ridge to toast s’mores and share stories of the day’s discoveries. As darkness falls, peer up at the sky to spot constellations and listen to a local elder recount ancient legends under a starry canopy.

day 2
Historic Downtown Discovery
morning
:

Stroll along cobblestone streets lined with restored Victorian-era storefronts and admire ornate ironwork balconies. Pop into the Hillside Heritage Museum to explore interactive exhibits on pioneer life and early railroad expansion. Grab a freshly baked pastry and locally roasted coffee from a family-run café around the corner.

afternoon
:

Join a guided walking tour through the historic district, stopping at hidden murals and century-old theaters with stories of bygone vaudeville performances. Drop into artisan boutiques where craftsmen demonstrate hand-carving, bookbinding, and stained-glass techniques. Enjoy a farm-to-table lunch at an intimate bistro that sources ingredients from nearby organic farms.

evening
:

Watch a live performance at the vintage Opera House, which hosts local musicians and touring theatrical troupes. After the show, dine on regional specialties—like heirloom bean stew and slow-roasted game—in an elegant candlelit setting. Conclude your evening with a moonlit stroll past gaslamp posts that cast dancing shadows on brick sidewalks.

day 3
Riverside Trail & Picnic
morning
:

Begin with a gentle riverside kayak trip, gliding through misty waters flanked by alder and willow trees. Listen for the melodic calls of kingfishers diving for breakfast beneath overhanging branches. Pull ashore at a secluded sandbar for a stretch and a nature sketch session.

afternoon
:

Spread a checkered blanket in a sun-dappled meadow and feast on a gourmet picnic basket packed with artisanal cheeses, charcuterie, and freshly baked bread. Forage for wild berries under the guidance of a local naturalist who can identify edible varieties and share folklore about the land. Spend some time sketching or journaling as dragonflies flit across the water’s edge.

evening
:

Return by kayak under the soft glow of a setting sun, painting the riverbanks in pastel hues. Dock at the Riverside Grill for a dinner of grilled trout, roasted root vegetables, and crisp local cider. End the night with live acoustic music on the outdoor patio, serenading the gently flowing river.

day 4
Artisan Village Immersion
morning
:

Drive to a nearby hilltop village renowned for its thriving artisan community. Begin your day with a pottery workshop, molding and glazing your own keepsake under the guidance of a master potter. Sip on herbal tea while exploring handcrafted wares in sunlit studios.

afternoon
:

Participate in a plein-air painting class in the village sculpture garden, learning color-mixing techniques from a resident artist. Wander through open-air stalls where glassblowers, weavers, and leatherworkers demonstrate centuries-old crafts. Savor a wood-fired pizza topped with foraged mushrooms and local goat cheese at a courtyard café.

evening
:

Gather at the village amphitheater for an open-mic poetry reading and acoustic jam session featuring local talent. Sample artisanal brews and ciders while mingling with the craftsmen whose workshops line the narrow lanes. Under string lights, enjoy a communal dinner of seasonal vegetable ratatouille and fresh-baked focaccia, punctuated by laughter and impromptu performances.

day 5
Hidden Waterfall Quest
morning
:

Set out on a private off-trail hike led by a guide who knows the secret paths to Hillside’s most secluded waterfall. Trek through fern-carpeted groves while listening to the distant roar of cascading water. Pause for a mindfulness session on a mossy log, breathing in the earthy scent of damp soil.

afternoon
:

Arrive at the waterfall’s tiered plunge pool, where you can take a refreshing swim in crystalline waters. Enjoy a picnic lunch of smoked salmon wraps, seasonal salads, and chilled lemonade on sun-warmed rocks. Practice landscape photography or watercolor painting to capture the waterfall’s dynamic beauty.

evening
:

Return along a different ridge to catch sweeping valley views at twilight. Warm up around a riverside campfire with a gourmet foil packet dinner featuring local trout and roasted root vegetables. As night falls, use lanterns to guide you back, relishing the hush of the forest after sunset.

day 6
Hilltop Vineyard and Wine Tasting
morning
:

Drive up to Suncrest Vineyards, perched on a gentle hillside overlooking rolling vineyards. Take part in a guided walking tour of the vines, learning about soil types, grape varieties, and sustainable farming practices. Sample freshly pressed grape juice and discuss harvest techniques with the vintner.

afternoon
:

Settle in for an elevated tasting experience in the barrel room, where aged reds and crisp whites are paired with artisanal cheeses and charcuterie. Learn to swirl, sniff, and savor under the guidance of a certified sommelier. Stroll through lavender fields adjacent to the vineyard, breathing in fragrant blooms.

evening
:

Watch the sun dip below the vine-laced horizon from a shaded terrace, then sit down for a multi-course dinner featuring locally sourced ingredients and wine pairings. Dine on herb-crusted lamb, truffle polenta, and a decadent dark-chocolate mousse. End the night with a moonlit walk among vine rows, where fireflies flicker like tiny lanterns.

day 7
Local Farm Experience
morning
:

Rise early at Maple Grove Farm to join in the morning chores—feeding chickens, gathering eggs, and checking on dairy goats. Learn milking techniques and taste freshly drawn cream straight from the source. Sip a robust farmhouse espresso while watching the sunrise over amber fields.

afternoon
:

Head to the farm kitchen for a cooking workshop with the resident chef, transforming your morning harvest into a savory farm-to-table lunch. Roll out homemade pasta, toss a fresh garden salad, and bake a rustic apple galette using hand-picked fruit. Share a communal meal outdoors beneath a shady apple tree.

evening
:

Return to the farm’s open-air barn where a lively barn dance unfolds under string lights. Kick up your heels to the tunes of a local folk band and learn traditional dances guided by friendly hosts. End the evening with s’mores by the bonfire and hearty cups of hot cider.

day 8
Nature Photography Workshop
morning
:

Gather at the Meadow View Lookout for a golden-hour photography session, capturing dew-kissed wildflowers bathed in soft morning light. A professional photographer provides tips on composition, focus, and exposure. End the session with a discussion on how to harness natural contrasts in your images.

afternoon
:

Settle in at a rustic studio space for a hands-on editing workshop, learning to enhance colors, balance shadows, and correct perspectives. Review your morning shots alongside fellow enthusiasts and receive personalized feedback. Enjoy a light lunch of grain bowls and herbal infusions while swapping photography stories.

evening
:

Attend a pop-up gallery exhibition featuring local photographers’ work paired with small bites and local wines. Mingle with artists and curators as you admire framed landscapes, macro details, and candid wildlife portraits. Leave with printed snapshots of your own best shots, ready to frame at home.

day 9
Stargazing Park Adventure
morning
:

Enjoy a leisurely brunch at The Overlook Café, sampling cloudberry pancakes and freshly squeezed juices. Spend some time browsing their reading nook filled with astronomy guides and local geology books. Pack a light daypack with snacks and a cozy blanket.

afternoon
:

Rest and recharge back at your accommodation with a nap or spa treatment before the evening’s celestial activities. Optional yoga session in a sunlit meadow prepares the body and mind for nighttime observation. Sip herbal tea while your guide sets up high-powered telescopes under a clear sky forecast.

evening
:

Head to Orion Park, a designated dark-sky preserve famous for minimal light pollution. Peer through telescopes to spot Jupiter’s cloud bands, Saturn’s rings, and distant star clusters. Toast marshmallows around a fire pit as a local astronomer narrates myths and scientific facts about the constellations above.

day 10
Farewell Feast & Cultural Showcase
morning
:

Begin with a serene hilltop yoga session at dawn, greeting the new day with gentle stretches and panoramic valley views. Follow it with a fresh-pressed fruit smoothie from a mobile juice bar parked nearby. Reflect on your journey in a short guided meditation.

afternoon
:

Wander through the Hillside Artisan Market one last time, handpicking souvenirs like handcrafted pottery, locally woven textiles, and small-batch jams. Chat with craft vendors to learn the stories behind their creations. Enjoy a light lunch picnic under a blooming cherry tree in the town square.

evening
:

Gather in the historic Pavilion for a grand farewell banquet, where chefs present a fusion menu celebrating Hillside’s culinary heritage. Watch traditional dance performances, folk music ensembles, and storytelling acts that highlight the region’s diverse culture. Raise a glass of sparkling cider in a final toast to new friendships and unforgettable memories.

Discover Hillside

Read more in our Hillside 2025 Travel Guide.

Hillside Travel Guide