Oakland
Oakland7days
7
Days
56
Activities
1
Location
21
Meals out
08:00
Earliest start

Luxury Outdoor Escape in Oakland

Experience the natural beauty and refined dining of Oakland, New Jersey, over seven well-paced days featuring forest hikes, lake kayaking, local market shopping, and educational arts centers.

  • 18Outdoors
  • 16Food stops
  • 6Museums
  • 6Markets & shops
  • 5Parks
  • 4Stays
  • couples
  • luxury
  • active travellers
  • nature
  • hiking
  • kayaking

Day by day

Day 1

Introduction to Oakland's Trails and Waters8 Activities

Begin your week exploring northern New Jersey's lush parks, scenic reservoir, and regional produce markets.

  1. 08:0009:00
    Food

    Breakfast at Oakland Diner

    08:00 – 09:00

    Enjoy an upscale morning meal with classic breakfast specialties and artisanal coffee.

  2. 09:3011:00
    Outdoor

    Scenic Hike at Ramapo Mountain State Forest

    09:30 – 11:00

    Embark on a guided morning hike through wooded trails offering panoramic ridge views.

  3. 11:1512:15
    Sightseeing

    Explore the New Weis Center for Education, Arts & Recreation

    11:15 – 12:15

    Visit the nature and arts facility to learn about regional ecology and historic conservation efforts.

    • entryFree
  4. 12:3013:30
    Food

    Lunch at Portobello Feasts

    12:30 – 13:30

    Dine on sophisticated Italian dishes and fresh seafood in an elegant setting.

  5. 14:0015:15
    Outdoor

    Kayaking on the Oakland Reservoir

    14:00 – 15:15

    Paddles across the calm waters of the reservoir surrounded by forested shoreline.

  6. 15:3016:45
    Shopping

    Shopping at Oakland Farmers' Market

    15:30 – 16:45

    Browse premium organic produce, artisanal cheeses, and local crafts.

  7. 17:0018:15
    Outdoor

    Visit the Great Oak Park

    17:00 – 18:15

    Take a relaxed afternoon stroll along manicured paths and open green lawns.

  8. 19:3021:00
    Food

    Dinner at Cenzino Ristorante

    19:30 – 21:00

    Savor fine Northern Italian dining accompanied by an extensive vintage wine list.

Day 2

Lakeside Relaxation and Forest Trails8 Activities

Spend the day immersed in Ramapo Valley's wilderness reserves and scenic community parks.

  1. 08:0009:00
    Food

    Breakfast at Caffe Capri

    08:00 – 09:00

    Start the day with fresh pastries, espresso, and warm breakfast entrees.

  2. 09:3011:00
    Outdoor

    Relax at Ramapo Valley County Reservation

    09:30 – 11:00

    Walk around Scarlet Oak Pond and enjoy tranquil lakeside mountain views.

  3. 11:1512:15
    Outdoor

    Kayaking on the Oakland Reservoir

    11:15 – 12:15

    Enjoy a peaceful mid-morning paddling session across the reservoir.

  4. 12:3013:30
    Food

    Lunch at Segovia Steakhouse & Seafood

    12:30 – 13:30

    Enjoy prime aged steaks and fresh Spanish-style seafood specialties.

  5. 14:0015:15
    Outdoor

    Scenic Hike at Ramapo Mountain State Forest

    14:00 – 15:15

    Follow the trail up to the historic castle ruins and overlooks.

  6. 15:3016:45
    Sightseeing

    Explore the New Weis Center for Education, Arts & Recreation

    15:30 – 16:45

    Attend an afternoon environmental talk or art exhibit in the main hall.

    • entryFree
  7. 17:0018:15
    Shopping

    Shopping at Oakland Farmers' Market

    17:00 – 18:15

    Pick up specialty baked goods and gourmet treats for late afternoon snacks.

  8. 19:3021:00
    Food

    Dinner at Trovato's Due

    19:30 – 21:00

    Relish classic Italian culinary craft paired with refined cocktails.

Day 3

Cultural Heritage and Park Exploration8 Activities

Combine arts, heritage education, and revitalizing park visits across Oakland.

  1. 08:0009:00
    Food

    Breakfast at The Market Basket Cafe

    08:00 – 09:00

    Sample fresh gourmet coffee, fruit, and handcrafted breakfast dishes.

  2. 09:3011:00
    Sightseeing

    Explore the New Weis Center for Education, Arts & Recreation

    09:30 – 11:00

    Take a guided outdoor walk focused on native flora and forest restoration.

    • entryFree
  3. 11:1512:15
    Outdoor

    Visit the Great Oak Park

    11:15 – 12:15

    Explore the park's scenic walking trails and historic oak tree groves.

  4. 12:3013:30
    Food

    Lunch at Yuki Hana

    12:30 – 13:30

    Enjoy high-end sushi and contemporary Japanese kitchen dishes.

  5. 14:0015:15
    Outdoor

    Relax at Ramapo Valley County Reservation

    14:00 – 15:15

    Unwind near the riverfront trails and quiet forest glades.

  6. 15:3016:45
    Shopping

    Shopping at Oakland Farmers' Market

    15:30 – 16:45

    Discover artisanal goods and fresh flower arrangements from local vendors.

  7. 17:0018:15
    Outdoor

    Kayaking on the Oakland Reservoir

    17:00 – 18:15

    Enjoy a tranquil late-afternoon paddle across calm lake waters.

  8. 19:3021:00
    Food

    Dinner at Cafe L'Amore

    19:30 – 21:00

    Experience gourmet Italian pasta dishes and chef specialties in an intimate setting.

Day 4

Active Waters and Mountain Heights8 Activities

Focus on outdoor activities with paddling, mountain hiking, and open parklands.

  1. 08:0009:00
    Food

    Breakfast at Lakeside Cafe

    08:00 – 09:00

    Fuel up with made-to-order omelets, French toast, and fresh juices.

  2. 09:3011:00
    Outdoor

    Kayaking on the Oakland Reservoir

    09:30 – 11:00

    Start the day with an invigorating morning kayak exploration on quiet waters.

  3. 11:1512:15
    Outdoor

    Scenic Hike at Ramapo Mountain State Forest

    11:15 – 12:15

    Tackle an elevated trail loop for sweeping woodland vistas.

  4. 12:3013:30
    Food

    Lunch at Trout Cafe

    12:30 – 13:30

    Savor seasonal soups, artisan sandwiches, and organic salads.

  5. 14:0015:15
    Outdoor

    Visit the Great Oak Park

    14:00 – 15:15

    Relax under the canopy of ancient trees and wander landscaped grounds.

  6. 15:3016:45
    Sightseeing

    Explore the New Weis Center for Education, Arts & Recreation

    15:30 – 16:45

    Tour the center's outdoor sensory trails and historic stone buildings.

    • entryFree
  7. 17:0018:15
    Outdoor

    Relax at Ramapo Valley County Reservation

    17:00 – 18:15

    Enjoy late afternoon bird watching and peaceful lake vistas.

  8. 19:3021:00
    Food

    Dinner at Biagio's Ristorante

    19:30 – 21:00

    Indulge in upscale Italian seafood and prime steak preparations.

Day 5

Local Markets and Nature Conservation8 Activities

A refined day of market browsing, nature talks, and scenic forest walks.

  1. 08:0009:00
    Food

    Breakfast at Java Love

    08:00 – 09:00

    Enjoy specialty pour-over coffee paired with house-baked pastries.

  2. 09:3011:00
    Shopping

    Shopping at Oakland Farmers' Market

    09:30 – 11:00

    Shop for farm-fresh fruit, honey, and handmade crafts in the morning market.

  3. 11:1512:15
    Outdoor

    Relax at Ramapo Valley County Reservation

    11:15 – 12:15

    Walk along the scenic Ramapo River bank and tranquil woodland paths.

  4. 12:3013:30
    Food

    Lunch at Portobello Feasts

    12:30 – 13:30

    Enjoy a relaxed lunch featuring wood-fired pizza and fresh salads.

  5. 14:0015:15
    Outdoor

    Scenic Hike at Ramapo Mountain State Forest

    14:00 – 15:15

    Take a moderate afternoon walk through quiet pine groves and overlooks.

  6. 15:3016:45
    Outdoor

    Kayaking on the Oakland Reservoir

    15:30 – 16:45

    Enjoy a mid-afternoon kayak session taking in late summer greenery.

  7. 17:0018:15
    Outdoor

    Visit the Great Oak Park

    17:00 – 18:15

    Stroll through peaceful gardens and open grassy fields as evening approaches.

  8. 19:3021:00
    Food

    Dinner at Segovia Steakhouse & Seafood

    19:30 – 21:00

    Relish fine steaks, lobster, and sangria in a comfortable luxury atmosphere.

Day 6

Arts, Heritage, and Mountain Trails8 Activities

Revisit favorite outdoor and cultural spots with fresh trails and new exhibitions.

  1. 08:0009:00
    Food

    Breakfast at Oakland Diner

    08:00 – 09:00

    Enjoy a hearty breakfast menu featuring freshly squeezed juices and gourmet dishes.

  2. 09:3011:00
    Outdoor

    Scenic Hike at Ramapo Mountain State Forest

    09:30 – 11:00

    Hike the northern ridge trail section for sweeping valley perspectives.

  3. 11:1512:15
    Shopping

    Shopping at Oakland Farmers' Market

    11:15 – 12:15

    Browse local artisan goods and regional souvenirs.

  4. 12:3013:30
    Food

    Lunch at Trovato's Due

    12:30 – 13:30

    Dine on Italian classics and chef-curated pasta creations.

  5. 14:0015:15
    Sightseeing

    Explore the New Weis Center for Education, Arts & Recreation

    14:00 – 15:15

    Participate in an afternoon eco-workshop and gallery viewing.

    • entryFree
  6. 15:3016:45
    Outdoor

    Relax at Ramapo Valley County Reservation

    15:30 – 16:45

    Enjoy a restful walk around MacMillan Reservoir.

  7. 17:0018:15
    Outdoor

    Kayaking on the Oakland Reservoir

    17:00 – 18:15

    Take a tranquil late-afternoon kayak tour around the lake islands.

  8. 19:3021:00
    Food

    Dinner at Cenzino Ristorante

    19:30 – 21:00

    Celebrate the evening with chef signature entrees and high-end wines.

Day 7

Grand Nature Finale in Oakland8 Activities

Conclude your week with a full sweep of Oakland's premier lakes, forests, and luxury dining.

  1. 08:0009:00
    Food

    Breakfast at Caffe Capri

    08:00 – 09:00

    Enjoy a final morning espresso with gourmet breakfast sandwiches.

  2. 09:3011:00
    Outdoor

    Relax at Ramapo Valley County Reservation

    09:30 – 11:00

    Take a serene morning stroll beside Scarlet Oak Pond.

  3. 11:1512:15
    Outdoor

    Visit the Great Oak Park

    11:15 – 12:15

    Enjoy the morning quiet along paved walking paths and shaded lawns.

  4. 12:3013:30
    Food

    Lunch at Yuki Hana

    12:30 – 13:30

    Savor fresh sashimi, specialty rolls, and delicate green tea ice cream.

  5. 14:0015:15
    Outdoor

    Kayaking on the Oakland Reservoir

    14:00 – 15:15

    Paddle out for one final scenic session on the water.

  6. 15:3016:45
    Shopping

    Shopping at Oakland Farmers' Market

    15:30 – 16:45

    Pick up last-minute organic preserves and handmade souvenirs.

  7. 17:0018:15
    Sightseeing

    Explore the New Weis Center for Education, Arts & Recreation

    17:00 – 18:15

    Walk through the outdoor sculpture trail and peaceful gardens.

    • entryFree
  8. 19:3021:00
    Food

    Dinner at Cafe L'Amore

    19:30 – 21:00

    Conclude your trip with romantic, fine-dining Italian cuisine and dessert.

Make it yours