Upper Montclair

Day Trips

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

day 1
Exploring the Local Community
morning
:

Start your day with a visit to the Upper Montclair's farmer's market, where you can sample fresh produce and local artisanal goods. Engage with friendly farmers and vendors to learn about the best seasonal ingredients. Grab a coffee from a nearby café to energize your morning stroll.

afternoon
:

Spend the afternoon exploring the charming boutiques along Bellevue Avenue, where you can find unique gifts and stylish fashion. Stop for lunch at a cozy eatery that serves delicious sandwiches and salads made from local ingredients. Don’t forget to visit the Montclair Art Museum, which features contemporary art and offers educational programs.

evening
:

As the evening approaches, unwind at Nishuane Park, where you can enjoy a leisurely walk or have a picnic. Consider dining at one of the area's upscale restaurants that offer a seasonally inspired menu. After dinner, catch a live performance or concert at one of the local venues for a night filled with entertainment.

day 2
Nature and Art Immersion
morning
:

Kick off your day with a serene hike at the nearby Eagle Rock Reservation, where you can take in panoramic views and enjoy the tranquility of nature. Breathe in the fresh air as you meander through the scenic trails that showcase the beauty of the local flora and fauna. After your hike, treat yourself to breakfast at a popular local diner known for its hearty meals.

afternoon
:

In the afternoon, visit the Craftsman Farms, the former home of architect Gustav Stickley, to learn about the Arts and Crafts Movement. Attend a workshop or take a guided tour to appreciate the intricate design and craftsmanship. Following your visit, enjoy lunch at a café in the vibrant Montclair town center.

evening
:

As the sun sets, explore the diverse dining scene in Upper Montclair, from Italian trattorias to modern American cuisine. After dinner, stroll through the local park or along the streets lined with vintage homes, taking in the picturesque neighborhood. Finish your day with a glass of wine at a local wine bar, enjoying the peaceful ambiance.

day 3
Cultural Excursions
morning
:

Start your day with a workshop at the Montclair Art Museum, where you can unleash your creativity while learning from skilled artists. The museum often provides guided tours that delve into its impressive collection, perfect for art enthusiasts. Enjoy a light breakfast at the museum café, tapping into the artistic vibe before your day unfolds.

afternoon
:

In the afternoon, immerse yourself in Upper Montclair’s history with a visit to the Montclair Historical Society. Discover the stories behind local artifacts and exhibitions that highlight the town's rich heritage. Savor a leisurely lunch at a nearby bistro that prides itself on locally sourced ingredients.

evening
:

For the evening, catch a theatrical performance at the Wellmont Theater, known for hosting a range of shows from local productions to well-known artists. Grab dinner at a nearby restaurant specializing in farm-to-table cuisine to complement your cultural experience. After the show, enjoy dessert at a local bakery that offers delicious treats.

day 4
Family Fun Day
morning
:

Begin your family adventure at the Turtle Back Zoo, where children can explore and learn about diverse wildlife. The zoo provides engaging exhibits and interactive experiences, making it a perfect morning outing. Afterward, enjoy a picnic brunch at the adjacent Essex County South Mountain Reservation for a relaxing atmosphere.

afternoon
:

In the afternoon, head over to the Montclair Community Pool or the local playground for some family-friendly fun and physical activity. Organize games like frisbee or soccer to keep the energy high. Visit the nearby family-owned ice cream shop afterward to cool down with delicious, handcrafted flavors.

evening
:

Conclude your day with a family dinner at a restaurant that offers a kid-friendly menu in a welcoming environment. Enjoy some quality time with board games or storytelling back at your accommodation, fostering cherished family memories. Wind down with a movie night featuring family classics to wrap up your adventure.

day 5
Sporting and Relaxation
morning
:

Start your day with a round of golf at one of Upper Montclair’s renowned golf courses, where you can enjoy the beautifully manicured greens. Golfers of all levels are welcomed, and the early morning hours offer a peaceful atmosphere. Follow up with a hearty breakfast at the clubhouse, discussing the highlights of your game.

afternoon
:

After golf, relax at a local spa for an afternoon of pampering treatments, including massages and facials designed to rejuvenate you. Embrace the tranquility and let the stress of daily life melt away during your indulgent spa experience. Post-spa, enjoy lunch at a nearby café that focuses on healthy and delicious options.

evening
:

In the evening, task yourself with attending a local sports event, whether it's high school football or community soccer matches, for an energetic and spirited ambiance. Cheer for the home team and experience the community spirit that Upper Montclair offers. As the night winds down, find a cozy spot to enjoy a nightcap and reflect on the day’s adventures.

day 6
Culinary Journey
morning
:

Begin your culinary journey with a cooking class focusing on local cuisines, where you can learn to prepare traditional dishes with a modern twist. The class often includes a market visit to select fresh ingredients, making for an immersive experience. Enjoy your delicious creation for breakfast, coupled with a local beverage.

afternoon
:

After the cooking class, explore nearby specialty food shops that sell gourmet ingredients and artisanal baked goods. Sample various cheeses, chocolates, and locally crafted items as you stroll through the charming streets. For lunch, indulge at a restaurant known for its creative dishes that showcase seasonally available produce.

evening
:

In the evening, attend a food and wine pairing event hosted by a local winery or restaurant, allowing you to experience a curated selection of local flavors. Engage with local sommeliers to learn about the pairing process and discover new taste combinations. End your culinary day with a leisurely walk, reflecting on the delightful food and experiences you've enjoyed.

day 7
Retail Therapy and Relaxation
morning
:

Start your day with a visit to the Montclair Art Museum’s gift shop, where you can find unique art-inspired items perfect for souvenirs. Browse through locally-made crafts and artworks that embody the essence of the community. Enjoy a leisurely breakfast at a trendy café nearby, soaking in the artistic atmosphere.

afternoon
:

After breakfast, make your way to Upper Montclair's various retail boutiques for an afternoon of shopping therapy. From chic clothing stores to eclectic home décor shops, the area offers a diverse array of shopping options. Recharge with coffee and pastries at a quaint bakery between stops to keep your energy up.

evening
:

Wrap up your day with a visit to a nearby lounge for a relaxed dinner amid a cozy ambiance. Enjoy live music performances while indulging in craft cocktails or a selection of local wines to wind down. Put the cherry on top of your day by hitting an ice cream parlor for an evening treat before heading back.

day 8
Historical Landmarks and Culture
morning
:

Embark on a visit to the Van Vleck House & Gardens for a tranquil morning of exploring beautiful landscapes and historic architecture. The gardens are perfect for a peaceful morning walk among vibrant flowers and greenery. Enjoy light refreshments at the onsite café while appreciating the serene surroundings.

afternoon
:

In the afternoon, stroll through Montclair’s cultural district, stopping at historical sites and galleries that depict the area’s rich history. Spend time appreciating local artistry and learning more about the community's cultural contributions. Have lunch at one of the cultural district's many eateries known for showcasing diverse culinary options.

evening
:

In the evening, participate in a local history tour or lecture at the Montclair Historical Society to delve deeper into the area’s past. Discover fascinating stories and anecdotes that bring Upper Montclair's history to life. Finish your enriching day with dinner at a restaurant that emphasizes historical recipes or dishes from the region.

day 9
Final Adventure and Reflection
morning
:

Take your last morning to revisit your favorite spots around Upper Montclair, reflecting on the memories created during your stay. Consider going back to the farmer's market or local shops to gather any last-minute souvenirs. Enjoy a lazy breakfast at your favorite café, soaking in the ambiance one last time.

afternoon
:

Spend the afternoon relaxing at a scenic park, where you can have a leisurely walk or simply read a book under the trees. Capture some of your favorite moments with photographs that will remind you of your journey. Enjoy lunch at a food truck that offers rotating menus featuring bold and exciting flavors.

evening
:

As your adventure comes to an end, have a farewell dinner at a fine dining restaurant known for its exceptional service and exquisite dishes. Toast to your experiences with a local specialty drink and reminisce about your days spent in this charming community. End your evening with a peaceful stroll, appreciating the tranquil evening vibes of Upper Montclair.

Discover Upper Montclair

Read more in our Upper Montclair 2025 Travel Guide.

Upper Montclair Travel Guide